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

General Information of Drug (ID: DR1923)
Drug Name
Alprostadil
Synonyms
Alista; Alprostadil(Caverject); Alprostadilum; Alprox-TD; Befar (TN); Caverject; Femprox; Lipoprost; Liprostin; MR-256; Minprog; Prink (TN); Prostaglandin E1; Prostandin; Prostavasin; Prostin VR; Prostin VR Pediatric; Prostivas; Topiglan; Vasaprostan; Vitaros; alprostadil; l-Prostaglandin E1; (11alpha,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid; (13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate; 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid; 745-65-3; Befar; CHEMBL495; Edex; Muse; PGE-1; PGE1; Prink; UNII-F5TD010360
Indication Erectile dysfunction [ICD11: HA01] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 354.5 Topological Polar Surface Area 94.8
Heavy Atom Count 25 Rotatable Bond Count 13
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5280723
PubChem SID
7312 ; 3139926 ; 4266050 ; 7847248 ; 7978676 ; 8143220 ; 8616376 ; 12013405 ; 14901054 ; 14901056 ; 24887977 ; 24890439 ; 24898661 ; 24898855 ; 24898994 ; 26719695 ; 26752225 ; 26752226 ; 39289772 ; 46386879 ; 46386882 ; 46387002 ; 47216549 ; 47515087 ; 47515088 ; 47810514 ; 47959471 ; 48110217 ; 48184750 ; 48415538 ; 49681576 ; 49699251 ; 50104916 ; 50104917 ; 53790811 ; 57357853 ; 57654538 ; 77812073 ; 85789478 ; 91702047 ; 92126041 ; 92308647 ; 92309224 ; 92309904 ; 92712130 ; 93166905 ; 99300818 ; 99302336 ; 103171219 ; 103914567
ChEBI ID
ChEBI:15544
CAS Number
745-65-3
TTD Drug ID
D0I4DQ
Formula
C20H34O5
Canonical SMILES
CCCCCC(C=CC1C(CC(=O)C1CCCCCCC(=O)O)O)O
InChI
1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
InChIKey
GMVPRGQOIOIIMI-DWKJAMRDSA-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
13,14-dihydro-prostaglandin E1 DM005379
161273
Unclear 1 [3] , [4] , [5]
15-keto-13,14-dihydro-prostaglandin E1 DM005378
165284
Unclear 1 [3] , [4] , [5] , [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005706 Alprostadil 15-keto-13,14-dihydro-prostaglandin E1 Unclear HPGD [3], [4], [5], [2]
MR005707 Alprostadil 13,14-dihydro-prostaglandin E1 Unclear Unclear [3], [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Prostaglandin dehydrogenase 1 (HPGD) DME0566 Homo sapiens
PGDH_HUMAN
1.1.1.141
[2]
References
1 Alprostadil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of calcium ionophore A23187 on prostaglandin synthase type 2 and 15-hydroxy-prostaglandin dehydrogenase expression in human chorion trophoblast cells. Am J Obstet Gynecol. 2008 Nov;199(5):554.e1-8.
3 Pharmacokinetics of prostaglandin E1 and its main metabolites after intracavernous injection and short-term infusion of prostaglandin E1 in patients with erectile dysfunction
4 Synergism between PGE1-metabolites(13,14-dihydro-prostaglandin E1, 15-keto prostaglandin E1, 15-keto-13,14-dihydro-prostaglandin E1) and nitric oxide (NO) on platelet aggregation
5 Pharmacokinetics of vasoactive substances administered into the human corpus cavernosum

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