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

General Information of Drug (ID: DR0807)
Drug Name
Heroin
Prodrug Info Heroin is the prodrug of Morphine
Synonyms
Acetomorfine; Acetomorphine; Amsterdam Marble; Aspron; Diacephin; Diacetyl morphine; Diacetylmorfin; Diacetylmorphine; Diamorfina; Diamorphine; Diaphorm; Diasetielmorfien; Diasetilmorfin; Diasetylmorfiimi; Diazetylmorphine; Eroina; HEROIN; Heroien; Heroiin; Herolan; Iroini; Malaysian Pink; Morphacetin; Morphine diacetate; O,O'-Diacetylmorphine; Persian; Persian brown; TNT (narcotic); White junk; White stuff; 3,6-Diacetylmorphine; 3,6-O-Diacetylmorphine; 561-27-3; Crap; Dooje; Dujie; Hairy; Harry; Horse; Junk; Preza; Rufus; Scot; Smack; Stuff
Indication Opiate dependence [ICD11: 6C43] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 369.4 Topological Polar Surface Area 65.099
Heavy Atom Count 27 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5462328
PubChem SID
8764 ; 841230 ; 11533163 ; 11688544 ; 14803926 ; 15375034 ; 24895466 ; 39459487 ; 46506839 ; 49992771 ; 51091623 ; 53788776 ; 57363457 ; 57654237 ; 78295149 ; 103607696 ; 127272440 ; 127272441 ; 127272442 ; 127272443 ; 127272444 ; 127272445 ; 127272446 ; 127272447 ; 127272448 ; 128011355 ; 134977824 ; 137001239 ; 137174640 ; 144206165 ; 160964715 ; 162221988 ; 162264004 ; 164842106 ; 175268259 ; 179293292 ; 184548227 ; 198993338 ; 226421461
ChEBI ID
ChEBI:27808
CAS Number
561-27-3
TTD Drug ID
D0T6WT
Formula
C21H23NO5
Canonical SMILES
CC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)OC(=O)C)CCN3C
InChI
1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
InChIKey
GVGLGOZIDCSQPN-PVHGPHFFSA-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-Monoacetylmorphine DM003207
5462507
Oxidation - Deacetylation 1 [3]
Morphine DM003208
60053788
Oxidation - Deacetylation 2 [3]
Codeine DM003212
5284371
Conjugation - Methylationn 3 [5]
Morphine ethereal sulfate DM003213 N. A. Conjugation - Sulfation 3 [5]
Morphine glucuronide DM003209
5360621
Conjugation - Glucuronidation 3 [4]
Morphine-3-glucuronide DM003210 N. A. Conjugation - Glucuronidation 3 [4]
Normorphine DM003211
5462508
Oxidation - Demethylation 3 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013330 Heroin 6-Monoacetylmorphine Oxidation - Deacetylation CES1 ... [3]
MR013331 6-Monoacetylmorphine Morphine Oxidation - Deacetylation CES1 ... [3]
MR013332 Morphine Morphine-6-glucuronide Conjugation - Glucuronidation UGT1A1 ... [4]
MR013333 Morphine Morphine-3-glucuronide Conjugation - Glucuronidation UGT1A1 ... [4]
MR013334 Morphine Normorphine Oxidation - Demethylation Unclear [5]
MR013335 Morphine Codeine Conjugation - Methylationn Unclear [5]
MR013336 Morphine Morphine ethereal sulfate Conjugation - Sulfation Unclear [5]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Acetylcholinesterase (ACHE) DME0058 Homo sapiens
ACES_HUMAN
3.1.1.7
[2]
Butyrylcholine esterase (BCHE) DME0069 Homo sapiens
CHLE_HUMAN
3.1.1.8
[3]
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[3]
Carboxylesterase 2 (CES2) DME0057 Homo sapiens
EST2_HUMAN
3.1.1.1
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A10 (UGT1A10) DME0075 Homo sapiens
UD110_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME0049 Homo sapiens
UDB15_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B17 (UGT2B17) DME0066 Homo sapiens
UDB17_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4]
⏷ Show the Full List of 13  DME(s)
References
1 ClinicalTrials.gov (NCT00175357) NAOMI: A Study to Compare Medically-prescribed Heroin With Oral Methadone in Chronic Opiate Addiction.
2 Kinetic characterization of cholinesterases and a therapeutically valuable cocaine hydrolase for their catalytic activities against heroin and its metabolite 6-monoacetylmorphine. Chem Biol Interact. 2018 Sep 25;293:107-114.
3 Metabolism of cocaine and heroin is catalyzed by the same human liver carboxylesterases
4 PharmGKB:Heroin
5 Morphine: pharmacokinetics and clinical practice

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