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

General Information of Drug (ID: DR0679)
Drug Name
Famciclovir
Prodrug Info Famciclovir is the prodrug of Penciclovir
Synonyms
Famciclovir (Famvir); Famciclovirum; Famciclovirum [INN-Latin]; Famvir; Anti-Farnesyl Rabbit pAb; GGXKWVWZWMLJEH-UHFFFAOYSA-N; QIC03ANI02; famciclovir; 1,3-Propanediol, 2-(2-(2-amino-9H-purin-9-yl)ethyl)-, diacetate (ester); 104227-87-4; 2-(2-(2-Amino-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate; 2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate; 9-[4-acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurine; BRL 42810; BRL-42810; CHEBI:4974; FCV; UNII-QIC03ANI02; [2-(acetyloxymethyl)-4-(2-aminopurin-9-yl)butyl] acetate
Indication Genital herpes [ICD11: 1A94] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 321.33 Topological Polar Surface Area 122
Heavy Atom Count 23 Rotatable Bond Count 9
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
3324
PubChem SID
626303 ; 5276651 ; 7847383 ; 7979216 ; 8152111 ; 11363360 ; 11365922 ; 11368484 ; 11372808 ; 11374301 ; 11376646 ; 11484938 ; 11488917 ; 11491490 ; 11492426 ; 11494280 ; 11528705 ; 12013946 ; 14899331 ; 26612822 ; 26680213 ; 26719883 ; 26748972 ; 26748973 ; 26758694 ; 29222459 ; 46386745 ; 46507561 ; 47291220 ; 47515410 ; 48415997 ; 49681753 ; 50107498 ; 52712677 ; 53800778 ; 56313627 ; 57321725 ; 68530529 ; 81092805 ; 85173809 ; 85787983 ; 92124793 ; 92308042 ; 92308372 ; 92309126 ; 92710468 ; 103158204 ; 103231964 ; 104253634 ; 104303176
ChEBI ID
CHEBI:4974
CAS Number
104227-87-4
TTD Drug ID
D0VT8P
Formula
C14H19N5O4
Canonical SMILES
CC(=O)OCC(CCN1C=NC2=CN=C(N=C21)N)COC(=O)C
InChI
1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)
InChIKey
GGXKWVWZWMLJEH-UHFFFAOYSA-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
6-deoxy monoacetylated penciclovir DM000142 N. A. Conjugation - Acetylation 1 [3]
6-deoxy penciclovir DM000138
128517
Oxidation - Dideacetylation 1 [3]
Monoacetylated penciclovir DM000141 N. A. Conjugation - Acetylation 1 [3]
Penciclovir DM000139
135398748
Oxidation - Deacetylation 1 [3]
Penciclovir DM000139
135398748
Oxidation - Oxidation 2 [3]
Penciclovir-triphosphate DM000140
135434855
Other reaction - Phosphorylation 2 [3]
Penciclovir-triphosphate DM000140
135434855
Other reaction - Phosphorylation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003088 Famciclovir 6-deoxy penciclovir Oxidation - Dideacetylation Unclear [3]
MR003089 Famciclovir Penciclovir Oxidation - Deacetylation Unclear [3]
MR003090 Famciclovir Monoacetylated penciclovir Conjugation - Acetylation Unclear [3]
MR003091 Famciclovir 6-deoxy monoacetylated penciclovir Conjugation - Acetylation Unclear [3]
MR003086 6-deoxy penciclovir Penciclovir Oxidation - Oxidation AOX1 [3]
MR003087 Penciclovir Penciclovir triphosphate Other reaction - Phosphorylation Unclear [3]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldehyde oxidase (AOX1) DME0052 Homo sapiens
AOXA_HUMAN
1.2.3.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1257 Bifidobacterium longum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1367 Bacteroides finegoldii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1470 Victivallis vadensis Not Available Not Available [4]
⏷ Show the Full List of 24  DME(s)
References
1 Famciclovir was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetic modeling of penciclovir and BRL42359 in the plasma and tears of healthy cats to optimize dosage recommendations for oral administration of famciclovir Am J Vet Res. 2016 Aug;77(8):833-45. doi: 10.2460/ajvr.77.8.833.
3 Evidence that famciclovir (BRL 42810) and its associated metabolites do not inhibit the 6 beta-hydroxylation of testosterone in human liver microsomes. Drug Metab Dispos. 1993 Jan-Feb;21(1):18-23.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.