Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2640)
Drug Name
BV-ara-U
Synonyms
BVaraU; Bravavir; Bravavir (TN); Bromovinyl araU; Bromovinyluridine; Brovavir; C11H13BrN2O6; C7VOZ162LV; CCRIS 5285; CHEBI:32152; CHEMBL70046; CS-0080932; D01734; DB11998; DRU-0136; HY-123032; JA-001; LS-135099; Q905418; SB18958; SCHEMBL82640; SO-32756; SORIVUDINE; SQ 32,756; SQ-32756; Sorivudina; Sorivudina [INN-Spanish]; Sorivudine (JAN/USAN/INN); Sorivudine [USAN:BAN:INN:JAN]; Sorivudine [USAN:INN:BAN:JAN]; Sorivudinum; Sorivudinum [INN-Latin]; UNII-C7VOZ162LV; Usevir; Usevir (TN); YN-72; ZINC3653374; (+)-1-beta-D-Arabinofuranosyl-5-((E)-2-bromovinyl)uracil; (E)-1-beta-D-Arabinofuranosyl-5-(2-bromoethenyl)-2,4(1H,3H)-pyrimidinedione; (E)-5-(2-Bromovinyl)-1-beta-D-arabinofuranosyluracil; (E)-5-(2-Bromovinyl)uridine; 1-.beta.-D-arabinofuranosyl-5-(2-bromovinyl)uracil; 1-beta-D-Arabinofuranosyl-(E)-5-(2-bromovinyl)uracil; 1-beta-D-arabinofuranosyl-5-(2-bromovinyl)uracil; 1-beta-D-arabinofuranosyl-E-5-(2-bromovinyl)uracil; 2,4(1H,3H)-Pyrimidinedione, 1-.beta.-D-arabinofuranosyl-5-[(1E)-2-bromoethenyl]-; 2,4(1H,3H)-Pyrimidinedione, 1-beta-D-arabinofuranosyl-5-(2-bromoethenyl)-, (E)-; 5-((E)-2-Bromo-vinyl)-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-hydroxy-1H-pyrimidin-2-one; 5-(2-bromovinyl)-1-beta-D-arabinofuranosyluracil; 5-Bromovinyl-araU; 5-[(1E)-2-bromoethenyl]-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione; 5-[(E)-2-bromovinyl]-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione; 77181-69-2; AKOS025149268; ARYS-01; AS-73022; BDBM50206491; BV ara-U; BV-Ara-U; BV-araU; BVAU
Indication Human immunodeficiency virus infection [ICD11: 1C60] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 349.13 Topological Polar Surface Area 119
Heavy Atom Count 20 Rotatable Bond Count 3
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5282192
PubChem SID
626315 ; 7848797 ; 7980638 ; 8616933 ; 12012808 ; 14900752 ; 16893378 ; 39315678 ; 50036052 ; 57358563 ; 77279719 ; 103265675 ; 113856648 ; 135012287 ; 137167326 ; 137246337 ; 179117134 ; 198957337 ; 224424237 ; 226461391 ; 241137006 ; 252671781
ChEBI ID
CHEBI:32152
CAS Number
77181-69-2
TTD Drug ID
D03TGJ
Formula
C11H13BrN2O6
Canonical SMILES
C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)C=CBr
InChI
1S/C11H13BrN2O6/c12-2-1-5-3-14(11(19)13-9(5)18)10-8(17)7(16)6(4-15)20-10/h1-3,6-8,10,15-17H,4H2,(H,13,18,19)/b2-1+/t6-,7-,8+,10-/m1/s1
InChIKey
GCQYYIHYQMVWLT-HQNLTJAPSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
BVU(bromovinyl uracil) DM002522
688297
Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000533 BV-ara-U BVU(bromovinyl uracil) Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Unclear metabolic mechanism (DME-unclear) DME1253 Bacteroides oleiciplenus Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1764 Bacteroides vulgatus Not Available Not Available [2]
References
1 ClinicalTrials.gov (NCT00002358) A Study of BV-araU in the Treatment of Varicella-Zoster Viral Disease (VZV) in HIV-Infected Children Who Have Not Had Success With or Who Cannot Take Other Treatments for VZV
2 Intestinal anaerobic bacteria hydrolyse sorivudine, producing the high blood concentration of 5-(E)-(2-bromovinyl)uracil that increases the level and toxicity of 5-fluorouracil. Pharmacogenetics. 1997 Feb;7(1):35-43.
3 Sorivudine and 5-fluorouracil; a clinically significant drug-drug interaction due to inhibition of dihydropyrimidine dehydrogenase Br J Clin Pharmacol. 1998 Jul;46(1):1-4. doi: 10.1046/j.1365-2125.1998.00050.x.

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