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{{Short description|Glycopeptide antibiotic used to treat various cancers}}
{{Drugbox {{Drugbox
| IUPAC_name = <nowiki>-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3--1,3-thiazol-2-yl]-1,3-thiazol-2-yl]ethylamino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-hydroxy-4-methyl-5-oxopentan-2-yl]amino]-1-(1H-imidazol-5-yl)-3-oxopropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] carbamate</nowiki> | IUPAC_name = (2''R'',3''S'',4''S'',5''R'',6''R'')-2-<nowiki/>{amino}-3-oxopropyl]-5-methyl-4-pyrimidinyl}carbonyl)amino]-3-<nowiki/>{propyl}carbamoyl)-2,4'-bi-1,3-thiazol-2'-yl]ethyl}amino)-3-hydroxy-1-oxo-2-butanyl]amino}-3-hydroxy-4-methyl-5-oxo-2-pentanyl]amino}-1-(1''H''-imidazol-5-yl)-3-oxopropyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2''H''-pyran-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2''H''-pyran-4-yl carbamate
|image = Pingyangmycin.svg | image = Pingyangmycin.svg
| width = 300 | width = 300

<!--Clinical data--> <!--Clinical data-->
| pregnancy_category = D | pregnancy_category = D
| legal_status = Rx-only | legal_status = Rx-only
| routes_of_administration = ], intraarterial, ], intratumoral | routes_of_administration = ], intra-arterial, ], intratumoral

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| metabolism = ] | metabolism = ]
| elimination_half-life = 1.3 hours | elimination_half-life = 1.3 hours
| excretion = ] (25-50%) | excretion = ] (25-50%)

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}} | CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 11116-32-8 | CAS_number = 11116-32-8
| CAS_supplemental = <br/>{{CAS|55658-47-4|(hydrochloride)}} | CAS_supplemental = <br/>{{CAS|55658-47-4|(hydrochloride)}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5DY91Y7601
| PubChem = 84046 | PubChem = 84046
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 75831 | ChemSpiderID = 8232875
| synonyms = Bleomycin A5

<!--Chemical data--> <!--Chemical data-->
| C=57 | H=89 | N=19 | O=21 | S=2 | C=57 | H=89 | N=19 | O=21 | S=2
| smiles = C(O)(NC(=O)(C)(O)(C)NC(=O)(NC(=O)c1nc(nc(N)c1C)(CC(N)=O)NC(N)C(N)=O)(O1O(CO)(O)(O)1O1O(CO)(O)(OC(N)=O)1O)c1ccn1)C(=O)NCCc1nc(cs1)-c1nc(cs1)C(=O)NCCCNCCCCN
| molecular_weight = 1440.56126
| smiles = CC1=C(N=C(N=C1N)C(CC(=O)N)NCC(C(=O)N)N)C(=O)NC(C(C2=CN=CN2)OC3C(C(C(C(O3)CO)O)O)OC4C(C(C(C(O4)CO)O)OC(=O)N)O)C(=O)NC(C)C(C(C)C(=O)NC(C(C)O)C(=O)NCCC5=NC(=CS5)C6=NC(=CS6)C(=O)NCCCNCCCCN)O
| InChI = 1S/C57H89N19O21S2/c1-22-35(73-48(76-46(22)61)27(14-33(60)80)68-15-26(59)47(62)86)52(90)75-37(43(28-16-65-21-69-28)95-56-45(41(84)39(82)31(17-77)94-56)96-55-42(85)44(97-57(63)92)40(83)32(18-78)93-55)53(91)70-24(3)38(81)23(2)49(87)74-36(25(4)79)51(89)67-13-8-34-71-30(20-98-34)54-72-29(19-99-54)50(88)66-12-7-11-64-10-6-5-9-58/h16,19-21,23-27,31-32,36-45,55-56,64,68,77-79,81-85H,5-15,17-18,58-59H2,1-4H3,(H2,60,80)(H2,62,86)(H2,63,92)(H,65,69)(H,66,88)(H,67,89)(H,70,91)(H,74,87)(H,75,90)(H2,61,73,76)
| InChIKey = QYOAUOAXCQAEMW-UHFFFAOYSA-N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C57H89N19O21S2/c1-22-35(73-48(76-46(22)61)27(14-33(60)80)68-15-26(59)47(62)86)52(90)75-37(43(28-16-65-21-69-28)95-56-45(41(84)39(82)31(17-77)94-56)96-55-42(85)44(97-57(63)92)40(83)32(18-78)93-55)53(91)70-24(3)38(81)23(2)49(87)74-36(25(4)79)51(89)67-13-8-34-71-30(20-98-34)54-72-29(19-99-54)50(88)66-12-7-11-64-10-6-5-9-58/h16,19-21,23-27,31-32,36-45,55-56,64,68,77-79,81-85H,5-15,17-18,58-59H2,1-4H3,(H2,60,80)(H2,62,86)(H2,63,92)(H,65,69)(H,66,88)(H,67,89)(H,70,91)(H,74,87)(H,75,90)(H2,61,73,76) | StdInChI =1S/C57H89N19O21S2/c1-22-35(73-48(76-46(22)61)27(14-33(60)80)68-15-26(59)47(62)86)52(90)75-37(43(28-16-65-21-69-28)95-56-45(41(84)39(82)31(17-77)94-56)96-55-42(85)44(97-57(63)92)40(83)32(18-78)93-55)53(91)70-24(3)38(81)23(2)49(87)74-36(25(4)79)51(89)67-13-8-34-71-30(20-98-34)54-72-29(19-99-54)50(88)66-12-7-11-64-10-6-5-9-58/h16,19-21,23-27,31-32,36-45,55-56,64,68,77-79,81-85H,5-15,17-18,58-59H2,1-4H3,(H2,60,80)(H2,62,86)(H2,63,92)(H,65,69)(H,66,88)(H,67,89)(H,70,91)(H,74,87)(H,75,90)(H2,61,73,76)/t23-,24+,25+,26-,27-,31-,32+,36-,37-,38-,39+,40+,41-,42-,43-,44-,45-,55+,56-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QYOAUOAXCQAEMW-UHFFFAOYSA-N | StdInChIKey = QYOAUOAXCQAEMW-UTXKDXHTSA-N
}} }}


'''Pingyangmycin''' (also known as '''Bleomycin A<sub>5</sub>''') is an ] ] belongs to ], which is produced by ''Streptomyces verticillus var. pingyangensis n.sp.'', a ] of '']''. It was discovered in 1969 at ] of ] in ], and was brought into clinical use in 1978.<ref>{{Cite journal | last1 = Lin | first1 = F. T. | last2 = Li | first2 = D. D. | last3 = Yang | first3 = X. P. | last4 = Li | first4 = Q. | last5 = Xue | first5 = Y. C. | last6 = Zhen | first6 = Y. S. | title = Antitumor activity and preclinical pharmacologic evaluation of pingyangmycin (author's transl) | journal = Zhonghua zhong liu za zhi &#92;Chinese journal of oncology&#93; | volume = 1 | issue = 3 | pages = 161–166 | year = 1979 | pmid = 95444}}</ref> '''Pingyangmycin''' (also known as '''bleomycin A<sub>5</sub>''') is an ] ] belonging to the ] family, which is produced by ''Streptomyces verticillus'' var.'' pingyangensis n.sp.'', a ] of '']''. It was discovered in 1969 at ] of ] in ], and was brought into clinical use in 1978.<ref>{{cite journal | vauthors = Lin FT, Li DD, Yang XP, Li Q, Xue YC, Zhen YS | title = | journal = Zhonghua Zhong Liu Za Zhi | volume = 1 | issue = 3 | pages = 161–6 | year = 1979 | pmid = 95444 }}</ref>


In China pingyangmycin has largely superseded bleomycin A<sub>2</sub> (commonly known as "bleomycin"), since it's more effective, costs less, is easier to get, can treat a larger varities of ]s (such as ] and ]) and causes less ] injury.<ref>{{Cite journal | last1 = Zheng | first1 = J. W. | last2 = Yang | first2 = X. J. | last3 = Wang | first3 = Y. A. | last4 = He | first4 = Y. | last5 = Ye | first5 = W. M. | last6 = Zhang | first6 = Z. Y. | doi = 10.1016/j.oraloncology.2009.02.011 | title = Intralesional injection of Pingyangmycin for vascular malformations in oral and maxillofacial regions: An evaluation of 297 consecutive patients | journal = Oral Oncology | volume = 45 | issue = 10 | pages = 872–876 | year = 2009 | pmid = 19628423| pmc = }}</ref><ref>{{Cite journal | last1 = Xu | first1 = H. Z. | last2 = Zhang | first2 = H. Y. | title = The isolation and identification of pingyangmycin (author's transl) | journal = Yao xue xue bao = Acta pharmaceutica Sinica | volume = 15 | issue = 10 | pages = 609–614 | year = 1980 | pmid = 6167140}}</ref> Even though it also results in ], unlike bleomycin, it's most serious ] is ], which is rare but may happen even in a low dose, and can be fatal.<ref>{{Cite journal | last1 = Shou | first1 = B. Q. | last2 = Mao | first2 = Z. | last3 = Zhang | first3 = S. L. | last4 = Yang | first4 = Z. | title = Allergy caused by minidose and low concentration Pingyangmycin: A case report | journal = Hua xi kou qiang yi xue za zhi = Huaxi kouqiang yixue zazhi = West China journal of stomatology | volume = 27 | issue = 5 | pages = 572–573 | year = 2009 | pmid = 19927737}}</ref> Besides, it causes more ] than bleomycin: the occurrence of this complication in patients is between 20% and 50%. In China, pingyangmycin has largely superseded bleomycin A<sub>2</sub> (commonly known as "bleomycin"), since according to Chinese sources it is more effective, costs less, is easier to get, can treat a larger variety of ]s (such as ] and ]) and causes less ] injury.<ref>{{cite journal | vauthors = Zheng JW, Yang XJ, Wang YA, He Y, Ye WM, Zhang ZY | title = Intralesional injection of Pingyangmycin for vascular malformations in oral and maxillofacial regions: an evaluation of 297 consecutive patients | journal = Oral Oncology | volume = 45 | issue = 10 | pages = 872–6 | date = October 2009 | pmid = 19628423 | doi = 10.1016/j.oraloncology.2009.02.011 }}</ref><ref>{{cite journal | vauthors = Xu HZ, Zhang HY | title = | journal = Yao Xue Xue Bao = Acta Pharmaceutica Sinica | volume = 15 | issue = 10 | pages = 609–14 | date = October 1980 | pmid = 6167140 }}</ref> Though pingyangmycin and bleomycin can each cause ], pingyangmycin's most serious ] - which it does not share with bleomycin - is ], which is rare, but may happen even in a low dose, and can be fatal.<ref>{{cite journal | vauthors = Shou BQ, Mao Z, Zhang SL, Yang Z | title = | journal = Hua Xi Kou Qiang Yi Xue Za Zhi = Huaxi Kouqiang Yixue Zazhi = West China Journal of Stomatology | volume = 27 | issue = 5 | pages = 572–3 | date = October 2009 | pmid = 19927737 }}</ref> In addition, it causes a higher incidence of ] than bleomycin; the occurrence of this complication in patients is between 20 and 50%.


==References== == References ==
{{reflist}} {{reflist}}


] ]
] ]
]

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Latest revision as of 04:22, 25 March 2024

Glycopeptide antibiotic used to treat various cancers Pharmaceutical compound
Pingyangmycin
Clinical data
Other namesBleomycin A5
Pregnancy
category
  • D
Routes of
administration		intravenous, intra-arterial, intramuscular, intratumoral
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolismamidase
Elimination half-life1.3 hours
Excretionrenal (25-50%)
Identifiers
IUPAC name
  • (2R,3S,4S,5R,6R)-2-{amino}-3-oxopropyl]-5-methyl-4-pyrimidinyl}carbonyl)amino]-3-{propyl}carbamoyl)-2,4'-bi-1,3-thiazol-2'-yl]ethyl}amino)-3-hydroxy-1-oxo-2-butanyl]amino}-3-hydroxy-4-methyl-5-oxo-2-pentanyl]amino}-1-(1H-imidazol-5-yl)-3-oxopropyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl carbamate
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.031.221 Edit this at Wikidata
Chemical and physical data
FormulaC57H89N19O21S2
Molar mass1440.57 g·mol
3D model (JSmol)
SMILES
  • C(O)(NC(=O)(C)(O)(C)NC(=O)(NC(=O)c1nc(nc(N)c1C)(CC(N)=O)NC(N)C(N)=O)(O1O(CO)(O)(O)1O1O(CO)(O)(OC(N)=O)1O)c1ccn1)C(=O)NCCc1nc(cs1)-c1nc(cs1)C(=O)NCCCNCCCCN
InChI
  • InChI=1S/C57H89N19O21S2/c1-22-35(73-48(76-46(22)61)27(14-33(60)80)68-15-26(59)47(62)86)52(90)75-37(43(28-16-65-21-69-28)95-56-45(41(84)39(82)31(17-77)94-56)96-55-42(85)44(97-57(63)92)40(83)32(18-78)93-55)53(91)70-24(3)38(81)23(2)49(87)74-36(25(4)79)51(89)67-13-8-34-71-30(20-98-34)54-72-29(19-99-54)50(88)66-12-7-11-64-10-6-5-9-58/h16,19-21,23-27,31-32,36-45,55-56,64,68,77-79,81-85H,5-15,17-18,58-59H2,1-4H3,(H2,60,80)(H2,62,86)(H2,63,92)(H,65,69)(H,66,88)(H,67,89)(H,70,91)(H,74,87)(H,75,90)(H2,61,73,76)/t23-,24+,25+,26-,27-,31-,32+,36-,37-,38-,39+,40+,41-,42-,43-,44-,45-,55+,56-/m0/s1
  • Key:QYOAUOAXCQAEMW-UTXKDXHTSA-N

Pingyangmycin (also known as bleomycin A5) is an antitumor glycopeptide antibiotic belonging to the bleomycin family, which is produced by Streptomyces verticillus var. pingyangensis n.sp., a variety of Streptomyces verticillus. It was discovered in 1969 at Pingyang County of Zhejiang Province in China, and was brought into clinical use in 1978.

In China, pingyangmycin has largely superseded bleomycin A2 (commonly known as "bleomycin"), since according to Chinese sources it is more effective, costs less, is easier to get, can treat a larger variety of cancers (such as breast cancer and liver cancer) and causes less lung injury. Though pingyangmycin and bleomycin can each cause pulmonary fibrosis, pingyangmycin's most serious side effect - which it does not share with bleomycin - is anaphylactic shock, which is rare, but may happen even in a low dose, and can be fatal. In addition, it causes a higher incidence of fever than bleomycin; the occurrence of this complication in patients is between 20 and 50%.

References

  1. Lin FT, Li DD, Yang XP, Li Q, Xue YC, Zhen YS (1979). "". Zhonghua Zhong Liu Za Zhi . 1 (3): 161–6. PMID 95444.
  2. Zheng JW, Yang XJ, Wang YA, He Y, Ye WM, Zhang ZY (October 2009). "Intralesional injection of Pingyangmycin for vascular malformations in oral and maxillofacial regions: an evaluation of 297 consecutive patients". Oral Oncology. 45 (10): 872–6. doi:10.1016/j.oraloncology.2009.02.011. PMID 19628423.
  3. Xu HZ, Zhang HY (October 1980). "". Yao Xue Xue Bao = Acta Pharmaceutica Sinica. 15 (10): 609–14. PMID 6167140.
  4. Shou BQ, Mao Z, Zhang SL, Yang Z (October 2009). "". Hua Xi Kou Qiang Yi Xue Za Zhi = Huaxi Kouqiang Yixue Zazhi = West China Journal of Stomatology. 27 (5): 572–3. PMID 19927737.
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