| Revision as of 21:22, 12 February 2011 editEdgar181 (talk | contribs)Extended confirmed users196,325 edits removed Category:Naphthoquinolines using HotCat← Previous edit |
Latest revision as of 13:16, 30 December 2024 edit undoTurboSuperA+ (talk | contribs)280 edits grammar, flowTags: Visual edit Mobile edit Mobile web edit Newcomer task Newcomer task: copyedit |
| (74 intermediate revisions by 54 users not shown) |
| Line 1: |
Line 1: |
|
|
|
|
|
{{Short description|Chemical compound}} |
|
|
{{Multiple issues| |
|
|
{{primary sources|date=June 2014}} |
|
|
{{third-party|date=June 2014}} |
|
|
{{notability|date=June 2014}} |
|
|
{{Peacock|date=June 2014}} |
|
|
}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = |
|
|
|
| Watchedfields = changed |
|
⚫ |
| verifiedrevid = 413559525 |
|
| IUPAC_name = (4a''S'',4b''R'',8''S'',10a''R'',10b''S'',12a''S'')-1,1,10a,12a-tetramethyl-8-(1-methylpyrrolidin-1-ium-1-yl)-3,4,4a,4b,5,7,8,9,10,10b,11,12-dodecahydro-2''H''-naphthoquinolin-1-ium diiodide |
|
| IUPAC_name = (4a''S'',4b''R'',8''S'',10a''R'',10b''S'',12a''S'')-1,1,10a,12a-tetramethyl-8-(1-methylpyrrolidin-1-ium-1-yl)-3,4,4a,4b,5,7,8,9,10,10b,11,12-dodecahydro-2''H''-naphthoquinolin-1-ium diiodide |
| ⚫ |
| synonyms = Chandonium iodide; HS-310 |
|
|
| image = candocuronium iodide.png |
|
| image = candocuronium iodide.png |
|
|
|
|
| CASNo_Ref = |
|
|
|
<!--Clinical data--> |
| ⚫ |
| InChI =InChI=1S/C26H46N2.2HI/c1-25-14-12-21(28(5)17-6-7-18-28)19-20(25)10-11-22-23(25)13-15-26(2)24(22)9-8-16-27(26,3)4;;/h10,21-24H,6-9,11-19H2,1-5H3;2*1H/p-2/t21-,22+,23-,24-,25-,26-;;/m0../s1 |
|
|
|
| tradename = |
| ⚫ |
| smiles = C12C(C(3(C)CCCC3)CC2)=CC4()1(CC5(C)4()CCC5(C)C.. |
|
|
⚫ |
| pregnancy_category = Not applicable |
| ⚫ |
| InChIKey = PVOAQHMVFYNJHZ-XDMKMBKMSA-L |
|
|
⚫ |
| legal_status = Discontinued from clinical development |
|
⚫ |
| routes_of_administration = IV |
|
|
|
|
|
<!--Pharmacokinetic data--> |
|
⚫ |
| bioavailability = 100% (IV){{citation needed|date=June 2014}} |
|
|
|
|
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
| CAS_number = 54278-85-2 |
|
| CAS_number = 54278-85-2 |
|
| ATC_prefix = |
|
| ATC_prefix = none |
|
| ATC_suffix = |
|
|
| PubChem = 71537 |
|
| PubChem = 71537 |
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
| DrugBank = |
|
|
|
| ChEMBL = 2106112 |
| ⚫ |
| ChemSpiderID= |
|
|
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| ⚫ |
| C=26 | H=46 | N=2 | I=2 |
|
|
|
| UNII_Ref = {{fdacite|changed|FDA}} |
|
| molecular_weight = 640.47 g/mol |
|
|
|
| UNII = SC80GNP08C |
| ⚫ |
| bioavailability = 100% (IV) |
|
|
⚫ |
| synonyms = Chandonium iodide; HS-310 |
|
| protein_bound = |
|
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
| metabolism = |
|
|
⚫ |
| ChemSpiderID = 64610 |
|
| elimination_half-life = |
|
|
|
|
|
| excretion = |
|
|
|
<!--Chemical data--> |
| ⚫ |
| pregnancy_category = not applicable |
|
|
⚫ |
| C=26 | H=46 | I=2 | N=2 |
| ⚫ |
| legal_status = discontinued from clinical development |
|
|
⚫ |
| smiles = ..C\53=C/C1(CC2(1CCC2(C)C)C)3(C)CC(4(C)CCCC4)C/5 |
| ⚫ |
| routes_of_administration = IV |
|
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
⚫ |
| StdInChI = 1S/C26H46N2.2HI/c1-25-14-12-21(28(5)17-6-7-18-28)19-20(25)10-11-22-23(25)13-15-26(2)24(22)9-8-16-27(26,3)4;;/h10,21-24H,6-9,11-19H2,1-5H3;2*1H/q+2;;/p-2/t21-,22+,23-,24-,25-,26-;;/m0../s1 |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
⚫ |
| StdInChIKey = GGAGIPMNQXAXNH-XDMKMBKMSA-L |
|
}} |
|
}} |
|
|
|
|
|
'''Candocuronium iodide''' (formerly recognized as chandonium or HS-310<ref name = Gandiha>{{cite journal | author = Gandiha A, Marshall IG, Paul D, Singh H | title = Neuromuscular and other blocking actions of a new series of mono and bisquaternary aza steroids | journal = J Pharm Phamacol | year = 1974 | volume = 26 | issue = 11 | month = Nov | pages = 871–877 | pmid = 4156557 | doi = }}</ref>) is the prototypical azasteroidal ] or ] in the category of non-depolarizing ]. Its potential adjunctive use in ] to facilitate endotracheal ] and to provide ] relaxation during ] or ] was briefly evaluated in clinical studies in India, but further development was discontinued because of attendant undesirable cardiovasular effects, primarily tachycardia that was no worse than but also not an improvement over the clinically established pancuronium.<ref>{{cite journal | author = Dasgupta D, Gupta KC, Vispute AV, Karandikar SM | title = Comparative clinical evaluation of chandonium iodide and pancuronium bromide as muscle relaxant | journal = J Postgrad Med | year = 1990| volume = 36 | month = Apr | issue = 2 | pages = 95–99 | pmid = 2151453 | doi = }}</ref><ref>{{cite journal | author = Dasgupta D, D'Souza M, Shah SJ, Gupta KC, Satoskar RS | title = Clinical evaluation of chandonium iodide as muscle relaxant | journal = Indian J Med Res | year = 1988| volume = 87 | month = Mar | issue = | pages = 298–302 | pmid = 3397166 | doi = }}</ref><ref>{{cite journal | author = Kumar D, Bhatia VK, Yajnik S, Gaur SP, Nityanand S | title = Clinical evaluation of chandonium iodide as a nondepolarising muscle relaxant | journal = Indian J Med Res | year = 1990| volume = 92 | month = Oct | issue = | pages = 367–370 | pmid = 2148735 | doi = }}</ref><ref>Suri YV (1984). Chandonium-iodide. New non-depolarising muscle relaxant. In: "Anaesthesiology. Clinical Pharmacology" Suri YV, Singh D (Eds.) New Delhi: Vani Educational Books; 28-35.</ref> Chandonium demonstrated a short duration and a rapid onset of action, with little or no ganglion blocking activity, and it was only slightly less potent than ].<ref name = Gandiha/> |
|
'''Candocuronium iodide''' (], formerly chandonium, HS-310)<ref name = Gandiha>{{cite journal |vauthors=Gandiha A, Marshall IG, Paul D, Singh H | title = Neuromuscular and other blocking actions of a new series of mono and bisquaternary aza steroids | journal = J Pharm Pharmacol |date=Nov 1974 | volume = 26 | issue = 11 | pages = 871–877 | pmid = 4156557 | doi = 10.1111/j.2042-7158.1974.tb09195.x| s2cid = 37704229 }}</ref> is an ] ]. It was clinically evaluated in India for use within ] for ] and for providing ] relaxation during surgery or ]. Its development was discontinued due to attendant cardiovascular effects, primarily ] that was about the same as the clinically established ].<ref>{{cite journal |vauthors=Dasgupta D, Gupta KC, Vispute AV, Karandikar SM | title = Comparative clinical evaluation of chandonium iodide and pancuronium bromide as muscle relaxant | journal = J Postgrad Med |date=Apr 1990| volume = 36 | issue = 2 | pages = 95–99 | pmid = 2151453 }}</ref><ref>{{cite journal |vauthors=Dasgupta D, D'Souza M, Shah SJ, Gupta KC, Satoskar RS | title = Clinical evaluation of chandonium iodide as muscle relaxant | journal = Indian J Med Res |date=Mar 1988| volume = 87 | pages = 298–302 | pmid = 3397166 }}</ref><ref>{{cite journal |vauthors=Kumar D, Bhatia VK, Yajnik S, Gaur SP, Nityanand S | title = Clinical evaluation of chandonium iodide as a nondepolarising muscle relaxant | journal = Indian J Med Res |date=Oct 1990| volume = 92 | pages = 367–370 | pmid = 2148735 }}</ref><ref>Suri YV (1984). Chandonium-iodide. New non-depolarising muscle relaxant. In: "Anaesthesiology. Clinical Pharmacology" Suri YV, Singh D (Eds.) New Delhi: Vani Educational Books; 28-35.</ref> Candocuronium demonstrated a short duration in the body, but a rapid onset of action. It had little to no ganglion blocking activity, with a greater potency than pancuronium.<ref name = Gandiha/> |
|
|
|
|
|
|
==Background== |
|
As noted with other well established neuromuscular blocking agents, chandonium preferentially antagonizes competitively the ] subtype of acetycholine receptors.<ref>{{cite journal | author = Harvey AL, Paul D, Rodger IW, Singh H | title = Actions of the ] chandonium iodide on guinea-pig ileum and vas deferens preparations | journal = J Pharm Pharmacol | year = 1976| volume = 28 | month = | issue = 8 | pages = 617–619 | pmid = 11309 | doi = }}</ref> The agent was developed by researchers in the laboratories of Harkishan Singh at the Panjab University in Chandigarh, India, as part of the ongoing search for the Holy Grail of ] agents: a non-depolarizing replacement for the most popular clinically used depolarizing agent, ] (]). |
|
As with other neuromuscular-blocking agents, candocuronium is a preferential competitive antagonist of ] acetylcholine receptors.<ref>{{cite journal |vauthors=Harvey AL, Paul D, Rodger IW, Singh H | title = Actions of the muscle relaxant chandonium iodide on guinea-pig ileum and vas deferens preparations | journal = J Pharm Pharmacol | year = 1976| volume = 28 | issue = 8 | pages = 617–619 | pmid = 11309 | doi = 10.1111/j.2042-7158.1976.tb02812.x| s2cid = 7700031 }}</ref> The agent was developed by the laboratory of Harkishan Singh, Panjab University, Chandigarh, India, as part of the search for a non-depolarizing replacement for the most popular clinical depolarizing agent, ] (]).{{citation needed|date=June 2014}} |
|
|
|
|
|
|
==Design of candocuronium== |
|
The ''mono''- and ''bis''-quaternary ] series of compounds (to which chandonium belongs) stems from the same principle that led to the invention of ] such as ], ] and ]: the use of the steroid skeleton to provide a somewhat rigid distance between the two quaternary ammoniumm centers with appendages incorporating fragments of choline or acetylcholine. The discovery program, initiated by Singh,<ref name= Singh>{{cite journal | author = Singh H, Paul D | title = Steroids and related studies. XXV. Chandonium iodide (17a-methyl-3beta-pyrrolidino-17a-aza-D-homoandrost-5-ene dimethiodide) and other quaternary ammonium steroid analogues | journal = J Chem Soc Perkin 1 | year = 1974| volume = 12 | issue = | pages = 1475–1479 | pmid = 4472321 | doi = }}</ref> initially led to the synthesis of a ''bis''-quaternary non-depolarizing agent labelled HS-342 (4,17a-dimethyl-4,17a-diaza-D-homo-5α-androstane dimethiodide) that was equipotent with tubocurarine and with one-third its duration of action but not suitable for further clinical evaluation.<ref>{{cite journal | author = Marshall IG, Paul D, Singh H | title = Some actions of 4,17a-dimethyl-4,17a-diaza-D-homo-5alpha-androstane dimethiodide (HS-342), a new neuromuscular blocking drug | journal = J Pharm Pharmacol | year = 1973| volume = 25 | month = Jun | issue = 6 | pages = 441–446 | pmid = 4146581 | doi = }}</ref><ref>{{cite journal | author = Marshall IG, Paul D, Singh H | title = The neuromuscular and other blocking actions of 4,17a-dimethyl-4,17a-diaza-d-homo-5 -androstane dimethiodide (HS-342) in the anaesthetized cat | journal = Eur J Pharmacol | year = 1973| volume = 22 | month = May | issue = 2 | pages = 129–134 | pmid = 4715215 | doi = }}</ref> |
|
The ''mono''- and ''bis''-quaternary azasteroid series of compounds to which candocuronium belongs are based on the same principle that led to aminosteroids such as ], ] and ]: use of the steroid skeleton to provide a somewhat rigid distance between the two quaternary ammonium centers, with appendages incorporating fragments of choline or acetylcholine. The discovery program initiated by Singh<ref name= Singh>{{cite journal |vauthors=Singh H, Paul D | title = Steroids and related studies. Part XXV. Chandonium iodide (17a-methyl-3β-pyrrolidino-17a-aza-D-homoandrost-5-ene dimethiodide) and other quaternary ammonium steroid analogues| journal =Journal of the Chemical Society, Perkin Transactions 1| year = 1974| volume = 12 | issue = 12| pages = 1475–1479 | pmid = 4472321 | doi = 10.1039/p19740001475}}</ref> initially led to the synthesis of the ''bis''-quaternary non-depolarizing agent HS-342 (4,17a-dimethyl-4,17a-diaza-D-homo-5α-androstane dimethiodide) that was equipotent with tubocurarine and with one-third its duration of action, but not suitable for further clinical evaluation.<ref>{{cite journal |vauthors=Marshall IG, Paul D, Singh H | title = Some actions of 4,17a-dimethyl-4,17a-diaza-D-homo-5alpha-androstane dimethiodide (HS-342), a new neuromuscular blocking drug | journal = J Pharm Pharmacol |date=Jun 1973| volume = 25 | issue = 6 | pages = 441–446 | pmid = 4146581 | doi = 10.1111/j.2042-7158.1973.tb09130.x| s2cid = 46013073 }}</ref><ref>{{cite journal |vauthors=Marshall IG, Paul D, Singh H | title = The neuromuscular and other blocking actions of 4,17a-dimethyl-4,17a-diaza-d-homo-5 -androstane dimethiodide (HS-342) in the anaesthetized cat | journal = Eur J Pharmacol |date=May 1973| volume = 22 | issue = 2 | pages = 129–134 | pmid = 4715215 | doi = 10.1016/0014-2999(73)90002-2}}</ref> Modifications of the HS-342 structure{{clarify|date=June 2014}} led to the synthesis of two related ], HS-347 and HS-310 (subsequently named chandonium, then candocuronium).<ref name = Gandiha/><ref name = Singh/> HS-347 was equipotent with tubocurarine but exhibited considerable ganglion blocking activity; candocuronium appeared to be suitably placed for clinical trials following encouraging preclinical evaluations.{{editorializing|date=June 2014}}<ref>{{cite journal |vauthors=Gandiha A, Marshall IG, Paul D, Rodger IW, Scott W, Singh H | title = Some actions of chandonium iodide, a new short-acting muscle relaxant, in anaesthetized cats and on isolated muscle preparations | journal = Clin Exp Pharmacol Physiol |date=Mar–Apr 1975 | volume = 2 | issue = 2 | pages = 159–170 | pmid = 237641 | doi = 10.1111/j.1440-1681.1975.tb01830.x| s2cid = 21840628 }}</ref><ref name = Teerapong>{{cite journal |vauthors=Teerapong P, Marshall IG, Harvey AL, Singh H, Paul D, Bhardwaj TR, Ahuja NK | title = The effects of dihydrochandonium and other chandonium analogues on neuromuscular and autonomic transmission | journal = J Pharm Pharmacol |date=Aug 1979| volume = 31 | issue = 8 | pages = 521–528 | pmid = 39992 | doi = 10.1111/j.2042-7158.1979.tb13576.x| s2cid = 37032460 }}</ref><ref>{{cite journal |vauthors=Singh H, Chaudhary AK | title = Pharmacokinetics and disposition of chandonium iodide in rat | journal = Indian J Exp Biol |date=May 1985 | volume = 23 | issue = 5 | pages = 253–257 | pmid = 4077122 }}</ref><ref>{{cite journal |vauthors=Singh H, Chaudhary AK | title = Pharmacokinetics and disposition of chandonium iodide in monkey | journal = Indian J Exp Biol |date=May 1985 | volume = 23 | issue = 5 | pages = 258–261 | pmid = 4077123 }}</ref> |
|
|
|
|
|
|
==Modifications to the candocuronium design== |
|
Modifications around the structure of HS-342 led to two other notable agents, HS-347 and HS-310 (subsequently named chandonium).<ref name = Gandiha/><ref name = Singh/> HS-347 was equipotent with tubocurarine but also exhibited considerable ganglion blocking activity, whereas chandonium appeared to be suitably placed for clinical trials following encouraging preclinical evaluations.<ref>{{cite journal | author = Gandiha A, Marshall IG, Paul D, Rodger IW, Scott W, Singh H | title = Some actions of chandonium iodide, a new short-acting muscle relaxant, in anaesthetized cats and on isolated muscle preparations | journal = Clin Exp Pharmacol Physiol | year = 1975 | volume = 2 | issue = 2 | month = Mar-Apr | pages = 159–170 | pmid = 237641 | doi = }}</ref><ref name = Teerapong>{{cite journal | author = Teerapong P, Marshall IG, Harvey AL, Singh H, Paul D, Bhardwaj TR, Ahuja NK | title = The effects of dihydrochandonium and other chandonium analogues on neuromuscular and autonomic transmission | journal = J Pharm Pharmacol | year = 1979| volume = 31 | month = Aug | issue = 8 | pages = 521–528 | pmid = 39992 | doi = }}</ref><ref>{{cite journal | author = Singh H, Chaudhary AK | title = Pharmacokinetics and disposition of chandonium iodide in rat | journal = Indian J Exp Biol | year = 1985 | volume = 23 | month = May | issue = 5 | pages = 253–257 | pmid = 4077122 | doi = }}</ref><ref>{{cite journal | author = Singh H, Chaudhary AK | title = Pharmacokinetics and disposition of chandonium iodide in monkey | journal = Indian J Exp Biol | year = 1985 | volume = 23 | month = May | issue = 5 | pages = 258–261 | pmid = 4077123 | doi = }}</ref> |
|
|
⚫ |
Candocuronium did not provide the desired profile,{{clarify|date=June 2014}} and a further extension of research was undertaken to overcome its limitations.{{clarify|date=June 2014}} This led to four more potentially useful compounds,{{editorializing|date=June 2014}} HS-692, HS-693, HS-704 and HS-705,{{clarify|date=June 2014}}<ref>{{cite journal |vauthors=Singh H, Bhardwaj TR, Ahuja NK, Paul D | title = Steroids and related studies. Part 44. 17a-Methyl-3β-(N-pyrrolidinyl)17a-aza-D-homo-5α-androstane bis(methiodide)(dihydrochandonium iodide) and certain other analogues of chandonium iodide| journal = Journal of the Chemical Society, Perkin Transactions 1| year = 1979 | pages = 305–307 | doi = 10.1039/P19790000305}}</ref> whose onset and duration were indistinguishable from candocuronium, but all demonstrated profound vagolytic effects and much weaker potencies than candocuronium.<ref name = Teerapong /> To improve on potency, further modifications of the candocuronium nucleus were undertaken,{{clarify|date=June 2014}} leading to the identification of yet another potentially useful compound, HS-626.<ref>{{cite journal |vauthors=Singh H, Bhardwaj TR, Paul D | title = Steroids and related studies. Part 48. A chandonium iodide analogue possessing an acetylcholine-like moiety| journal = Journal of the Chemical Society, Perkin Transactions 1| year = 1979 | pages = 2451 | doi = 10.1039/p19790002451}}</ref> Upon further preclinical evaluation,<ref>{{cite journal |vauthors=Marshall IG, Harvey AL, Singh H, Bhardwaj TR, Paul D | title = The neuromuscular and autonomic blocking effects of azasteroids containing choline or acetylcholine fragments | journal = J Pharm Pharmacol |date=Jul 1981 | volume = 33 | issue = 7 | pages = 451–457 | pmid = 6115032 | doi = 10.1111/j.2042-7158.1981.tb13831.x| s2cid = 26115020 }}</ref> HS-626 demonstrated a slightly more desirable neuromuscular-blocking profile than that of candocuronium, but its overall improvement was insufficient to warrant advancement to clinical testing. |
|
|
|
|
|
|
==Modifications at 3- and 16-positions of androstane nucleus== |
| ⚫ |
As already noted, chandonium still did not provide the desirable profile and a further extension of research was undertaken to overcome the limitations of chandonium. This led to four more promising compounds, HS-692, HS-693, HS-704 and HS-705.<ref>{{cite journal | author = Singh H, Bhardwaj TR, Ahuja NK, Paul D | title = | journal = J Chem Soc, Perk Trans I | year = 1979 | volume = | month = | issue = | pages = 305 | pmid = | doi = }}</ref> The onset and duration of these four agents were indinguishable from those of chandonium, but, unfortunately, all demonstrated profound vagolytic effects and much weaker potencies than those of chandonium.<ref name = Teerapong /> To improve on the potency, further modifications of the chandonium nucleus were undertaken, leading to the identification of yet another promising compound, HS-626.<ref>{{cite journal | author = Singh H, Bhardwaj TR, Paul D | title = | journal = J Chem Soc, Perk Trans I | year = 1979 | volume = | month = | issue = | pages = 2451 | pmid = | doi = }}</ref> Unfortunately, upon further preclinical evaluations in the cat and isolated preparations,<ref>{{cite journal | author = Marshall IG, Harvey AL, Singh H, Bhardwaj TR, Paul D | title = The neuromuscular and autonomic blocking effects of azasteroids containing choline or acetylcholine fragments | journal = J Pharm Pharmacol | year = 1981 | volume = 33 | month = Jul | issue = 7 | pages = 451–457 | pmid = 6115032 | doi = }}</ref> it was clearly evident that, although HS-626 demonstrated a slightly more desirable neuromuscular blocking profile than that of chandonium, the overall degree of improvement was insufficient to warrant advancement to clinical testing. |
|
|
⚫ |
The discovery of candocuronium led to numerous related neuromuscular-blocking agents with short durations of action but also having attendant undesirable cardiovascular effects. The Marshall group then explored other modifications at the 3- and 16-positions of the androstane nucleus,<ref>{{cite journal |vauthors=Jindal DP, Piplani P, Fajrak H, Prior C, Marshall IG | title = Synthesis and neuromuscular blocking activity of 16β-piperidinosteroidal derivatives | journal = Eur J Med Chem |date=Feb 2001 | volume = 36 | issue = 2 | pages = 195–202 | pmid = 11311750 | doi = 10.1016/s0223-5234(00)01205-8}}</ref><ref>{{cite journal |vauthors=Jindal DP, Piplani P, Fajrak H, Prior C, Marshall IG | title = Synthesis and neuromuscular blocking activity of 16β-N-methylpiperazino steroidal derivatives | journal = Eur J Med Chem |date=Nov 2002 | volume = 37 | issue = 11 | pages = 901–908 | pmid = 12446049 | doi = 10.1016/s0223-5234(02)01413-7}}</ref> and yielded an agent that can go through expanded evaluation to clinical testing. |
|
|
|
| ⚫ |
Overall, Singh's research group discovered and identified chandonium which spawned numerous related neuromuscular blocking agents with short durations of action but also attendant with undesirable cardiovascular effects. Subsequent further attempts to attain the intended goal led the group to explore other modifications at the 3 and 16 positions of the androstane nucleus,<ref>{{cite journal | author = Jindal DP, Piplani P, Fajrak H, Prior C, Marshall IG | title = Synthesis and neuromuscular blocking activity of 16β-piperidinosteroidal derivatives | journal = Eur J Med Chem | year = 2001 | volume = 36 | month = Feb | issue = 2 | pages = 195–202 | pmid = 11311750 | doi = }}</ref><ref>{{cite journal | author = Jindal DP, Piplani P, Fajrak H, Prior C, Marshall IG | title = Synthesis and neuromuscular blocking activity of 16β-N-methylpiperazino steroidal derivatives | journal = Eur J Med Chem | year = 2002 | volume = 37 | month = Nov | issue = 11 | pages = 901–908 | pmid = 12446049 | doi = }}</ref> but the admirable undaunted persistence has not yet yielded an agent worthy of expanded evaluation to clinical testing in this azasteroidal class of neuromuscular blocking agents. |
|
|
|
|
|
|
==References== |
|
==References== |
| Line 45: |
Line 67: |
|
|
|
|
|
{{Muscle relaxants}} |
|
{{Muscle relaxants}} |
|
|
{{Nicotinic acetylcholine receptor modulators}} |
|
|
|
|
<!--- Categories ---> |
|
|
|
|
|
|
{{DEFAULTSORT:Candocuronium Iodide}} |
|
{{DEFAULTSORT:Candocuronium Iodide}} |
|
] |
|
] |
|
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
] |
|
|
] |