Drug Information

General Information
Drug ID
DR00102
Drug Name
Dinoprostone
Synonyms
(15S)-Prostaglandin E2; (5Z,11-alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid; (5Z,11.alpha.,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid; (5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic; (5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid; (5Z,11alpha,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid; (5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate; (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dienoate; (5Z,13E,15S)-11alpha,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid; (E,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid; (Z)-7-[(1R,2R,3R)-3-Hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid; 5-Heptenoic acid, 7-(3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-(8CI); 7-(3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid; Alpha, PGE2; Alpha, Prostaglandin E2; BML1-F07; BMS-279654 & PGE2; Cervidil; Cervidil (TN); Dinoproston; Dinoprostona; Dinoprostona [INN-Spanish]; Dinoprostone (JAN/USP/INN); Dinoprostone Prostaglandin E2; Dinoprostone [USAN:INN:BAN:JAN]; Dinoprostone beta-Cyclodextrin Clathrate; Dinoprostonum; Dinoprostonum [INN-Latin]; E2 alpha, Prostaglandin; E2, Prostaglandin; E2alpha, Prostaglandin; Gel, Prepidil; L-7-(3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl)-5-heptenoic acid; L-PGE2; L-Prostaglandin E2; Minprositin E2; Minprostin E2; PGE2; PGE2 alpha; PGE2alpha; Prepidil; Prepidil (TN); Prepidil Gel; Propess; Propess (TN); Prostaglandin E2; Prostaglandin E2 alpha; Prostaglandin E2alpha; Prostarmon E2; Prostarmon E;Prostin E; Prostenon; Prostin; Prostin E2; Prostin E2 (TN); U 12062; U-12062; [3H]PGE2
Drug Type
Small molecular drug
Indication Medical abortion [ICD11:JA00.1] Approved [1]
Therapeutic Class
Prostaglandins
Structure
3D MOL 2D MOL
Formula
C20H32O5
Canonical SMILES
CCCCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O
InChI
InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
InChIKey
XEYBRNLFEZDVAW-ARSRFYASSA-N
CAS Number
CAS 363-24-6
Pharmaceutical Properties Molecular Weight 352.5 Topological Polar Surface Area 94.8
Heavy Atom Count 25 Rotatable Bond Count 12
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
XLogP
2.8
PubChem CID
5280360
PubChem SID
103176817 ,10321741 ,104017641 ,104046436 ,14778621 ,14900948 ,24898100 ,24898683 ,24898775 ,26753268 ,26753269 ,26753270 ,26759401 ,3139923 ,3727087 ,3863 ,39289526 ,4265954 ,439749 ,450259 ,46505549 ,47662021 ,47810515 ,47885164 ,48415907 ,50026789 ,50087222 ,50105678 ,50105679 ,53789659 ,56313306 ,56314112 ,56459056 ,57357707 ,599053 ,75054349 ,7847147 ,7979101 ,803734 ,8143217 ,85789494 ,85856640 ,8616235 ,92298396 ,92308753 ,92309906 ,92722489 ,99300820 ,99302338 ,99431525
ChEBI ID
ChEBI:15551
TTD Drug ID
D06FEA
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
2-Oct Transporter Info Organic cation transporter 2 Substrate [2]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [3]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [4]
OAT1 Transporter Info Organic anion transporter 1 Substrate [5]
OAT2 Transporter Info Organic anion transporter 2 Substrate [5]
OAT3 Transporter Info Organic anion transporter 3 Substrate [5]
OAT4 Transporter Info Organic anion transporter 4 Substrate [5]
OATP1A2 Transporter Info Organic anion transporting polypeptide 1A2 Substrate [6]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [7]
OATP1C1 Transporter Info Organic anion transporting polypeptide 1C1 Substrate [8]
OATP2A1 Transporter Info Organic anion transporting polypeptide 2A1 Substrate [9]
OATP2B1 Transporter Info Organic anion transporting polypeptide 2B1 Substrate [9]
OATP3A1 Transporter Info Organic anion transporting polypeptide 3A1 Substrate [10]
OATP4A1 Transporter Info Organic anion transporting polypeptide 4A1 Substrate [9]
OATP5A1 Transporter Info Organic anion transporting polypeptide 5A1 Substrate [11]
OSTalpha Transporter Info Organic solute transporter subunit alpha Substrate [12]
OSTalpha Transporter Info Organic solute transporter subunit alpha Substrate [12]
OSTbeta Transporter Info Organic solute transporter subunit beta Substrate [12]
OSTbeta Transporter Info Organic solute transporter subunit beta Substrate [12]
Drug-Transporter Activity Data
Drug-Transporter Activity Data 1-Oct Transporter Info Km =0.657 microM Proximal tubule (S2) cells-OCT1 [5]
2-Oct Transporter Info Km =0.0289 microM Proximal tubule (S2) cells-OCT2 [5]
MRP4 Transporter Info Km =3.4 microM Spodoptera frugiperda (Sf9) cells-MRP4 [4]
OAT1 Transporter Info Km =0.97 microM Proximal tubule (S2) cells-OAT1 [5]
OAT2 Transporter Info Km =0.713 microM Proximal tubule (S2) cells-OAT2 [5]
OAT3 Transporter Info Km =0.345 microM Proximal tubule (S2) cells-OAT3 [5]
OAT4 Transporter Info Km =0.154 microM Proximal tubule (S2) cells-OAT4 [5]
References
1 Dinoprostone was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Are organic cation transporters capable of transporting prostaglandins? Naunyn Schmiedebergs Arch Pharmacol. 2005 Aug;372(2):125-30.
3 Multidrug resistance associated protein 2 mediates transport of prostaglandin E2. Liver Int. 2006 Apr;26(3):362-8.
4 The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9.
5 Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8.
6 Localization of organic anion transporting polypeptide 4 (Oatp4) in rat liver and comparison of its substrate specificity with Oatp1, Oatp2 and Oatp3. Pflugers Arch. 2001 Nov;443(2):188-95.
7 Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
8 Identification of a novel human organic anion transporting polypeptide as a high affinity thyroxine transporter. Mol Endocrinol. 2002 Oct;16(10):2283-96.
9 Molecular identification and characterization of novel members of the human organic anion transporter (OATP) family. Biochem Biophys Res Commun. 2000 Jun 24;273(1):251-60.
10 Molecular characterization of human and rat organic anion transporter OATP-D. Am J Physiol Renal Physiol. 2003 Dec;285(6):F1188-97.
11 Expression and regulation of prostaglandin transporters, ATP-binding cassette, subfamily C, member 1 and 9, and solute carrier organic anion transporter family, member 2A1 and 5A1 in the uterine endometrium during the estrous cycle and pregnancy in pigs. Asian-Australas J Anim Sci. 2017 May;30(5):643-652.
12 Functional complementation between a novel mammalian polygenic transport complex and an evolutionarily ancient organic solute transporter, OSTalpha-OSTbeta. J Biol Chem. 2003 Jul 25;278(30):27473-82.

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