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Revision as of 14:03, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit Latest revision as of 15:40, 22 October 2024 edit undoCitation bot (talk | contribs)Bots5,428,502 edits Added pmid. | Use this bot. Report bugs. | Suggested by Dominic3203 | Category:Antihypertensive agent stubs | #UCB_Category 26/91 
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{{chembox {{chembox
| verifiedrevid = 443561394 | verifiedrevid = 443681733
|ImageFile=Debrisoquine.svg | ImageFile=Debrisoquine.svg
|ImageSize= | ImageSize=
|IUPACName=1,2,3,4-tetrahydroisoquinoline-2-carboximidamide | PIN=3,4-Dihydroisoquinoline-2(1''H'')-carboximidamide
|OtherNames= | OtherNames=
|Reference=<ref>, ].</ref> | Reference=<ref>, ].</ref>
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X31CDK040E | UNII = X31CDK040E
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
Line 21: Line 21:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=1131-64-2 | CASNo=1131-64-2
| PubChem=2966 | PubChem=2966
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2860 | ChemSpiderID = 2860
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 34665 | ChEBI = 34665
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB04840 | DrugBank = DB04840
| SMILES = =C(N)N2Cc1c(cccc1)CC2 | SMILES = =C(N)N2Cc1c(cccc1)CC2
| MeSHName=Debrisoquine | MeSHName=Debrisoquine
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>10</sub>H<sub>13</sub>N<sub>3</sub> | Formula=C<sub>10</sub>H<sub>13</sub>N<sub>3</sub>
| MolarMass=175.23032 | MolarMass=175.23032
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3={{Chembox Hazards |Section6={{Chembox Pharmacology
| ATCCode_prefix = C02
⚫ | MainHazards=
| ATCCode_suffix = CC04
⚫ | FlashPt=
}}
| Autoignition=
|Section7={{Chembox Hazards
⚫ | MainHazards=
⚫ | FlashPt=
| AutoignitionPt =
}} }}
}} }}


'''Debrisoquine''' is a derivative of ]. It is an ] drug similar to ]. Debrisoquine is frequently used for phenotyping the ] enzyme, a drug metabolizing enzyme.<ref> Appropriate Phenotyping Procedures for Drug Metabolizing Enzymes and Transporters in Humans and Their Simultaneous Use in the "Cocktail" Approach</ref> '''Debrisoquine''' is a derivative of ]. It is an ] drug similar to ]. Debrisoquine is frequently used for ] the ] enzyme, a drug-metabolizing enzyme.<ref>{{Cite journal | last1 = Fuhr | first1 = U. | last2 = Jetter | first2 = A. | last3 = Kirchheiner | first3 = J. | doi = 10.1038/sj.clpt.6100050 | title = Appropriate Phenotyping Procedures for Drug Metabolizing Enzymes and Transporters in Humans and Their Simultaneous Use in the "Cocktail" Approach | journal = Clinical Pharmacology & Therapeutics | volume = 81 | issue = 2 | pages = 270–283 | year = 2007 | pmid = 17259951 }}</ref>


Debrisoquine has been identified as a inhibitor of ] protease, which is involved in the ] process of ]. In a laboratory study, it showed antiviral activity by blocking the ability of the virus to enter human lung cells.<ref name="pmid37284689">{{cite journal |vauthors=Peiffer AL, Garlick JM, Wu Y, Wotring JW, Arora S, Harmata AS, Bochar DA, Stephenson CJ, Soellner MB, Sexton JZ, Brooks CL, Mapp AK |title=TMPRSS2 Inhibitor Discovery Facilitated through an In Silico and Biochemical Screening Platform |journal=ACS Medicinal Chemistry Letters |volume=14 |issue=6 |pages=860–866 |date=June 2023 |pmid=37284689 |pmc=10237299 |doi=10.1021/acsmedchemlett.3c00035}}</ref>
⚫ ==See also==
⚫ * ]


The ] part of the molecule also appears in ] and ].{{citation needed|date=August 2024}} The 7-bromo analog of debrisoquine is called ].{{citation needed|date=August 2024}}
⚫ ==References==
{{reflist}}


⚫ == See also ==
⚫ * {{section link|Isoquinoline|Applications of derivatives}}

⚫ == References ==
{{Reflist}}


{{Antihypertensives and diuretics}} {{Antihypertensives and diuretics}}


]
⚫ ]
] ]
] ]
⚫ ]




Latest revision as of 15:40, 22 October 2024

Debrisoquine
Names
Preferred IUPAC name 3,4-Dihydroisoquinoline-2(1H)-carboximidamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.013.155 Edit this at Wikidata
KEGG
MeSH Debrisoquine
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H13N3/c11-10(12)13-6-5-8-3-1-2-4-9(8)7-13/h1-4H,5-7H2,(H3,11,12)Key: JWPGJSVJDAJRLW-UHFFFAOYSA-N
  • InChI=1/C10H13N3/c11-10(12)13-6-5-8-3-1-2-4-9(8)7-13/h1-4H,5-7H2,(H3,11,12)Key: JWPGJSVJDAJRLW-UHFFFAOYAE
SMILES
  • =C(N)N2Cc1c(cccc1)CC2
Properties
Chemical formula C10H13N3
Molar mass 175.23032
Pharmacology
ATC code C02CC04 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Debrisoquine is a derivative of guanidine. It is an antihypertensive drug similar to guanethidine. Debrisoquine is frequently used for phenotyping the CYP2D6 enzyme, a drug-metabolizing enzyme.

Debrisoquine has been identified as a inhibitor of TMPRSS2 protease, which is involved in the viral entry process of SARS-CoV-2. In a laboratory study, it showed antiviral activity by blocking the ability of the virus to enter human lung cells.

The guanidine part of the molecule also appears in guanoxan and guanadrel. The 7-bromo analog of debrisoquine is called guanisoquin.

See also

References

  1. Debrisoquine – Compound Summary, PubChem.
  2. Fuhr, U.; Jetter, A.; Kirchheiner, J. (2007). "Appropriate Phenotyping Procedures for Drug Metabolizing Enzymes and Transporters in Humans and Their Simultaneous Use in the "Cocktail" Approach". Clinical Pharmacology & Therapeutics. 81 (2): 270–283. doi:10.1038/sj.clpt.6100050. PMID 17259951.
  3. Peiffer AL, Garlick JM, Wu Y, Wotring JW, Arora S, Harmata AS, Bochar DA, Stephenson CJ, Soellner MB, Sexton JZ, Brooks CL, Mapp AK (June 2023). "TMPRSS2 Inhibitor Discovery Facilitated through an In Silico and Biochemical Screening Platform". ACS Medicinal Chemistry Letters. 14 (6): 860–866. doi:10.1021/acsmedchemlett.3c00035. PMC 10237299. PMID 37284689.
Sympatholytic (and closely related) antihypertensives (C02)
Sympatholytics
(antagonize α-adrenergic
vasoconstriction)
Central
α2-Adrenergic receptor agonists
Adrenergic release inhibitors
Imidazoline receptor agonists
Ganglion-blocking/nicotinic antagonists
Peripheral
Indirect
Monoamine oxidase inhibitors
VMAT inhibitors
Tyrosine hydroxylase inhibitors
Direct
α1-Adrenergic receptor blockers
Non-selective α-adrenergic receptor blockers
Other antagonists
Serotonin receptor antagonists
Endothelin receptor antagonists (for PHTooltip Pulmonary hypertension)


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