Drug Information

General Information
Drug ID
DR00007
Drug Name
Prostaglandin f2Alpha
Synonyms
Amoglandin; Cerviprost; Cyclosin; Enzaprost; PGF2alpha; Panacelan
Drug Type
Small molecular drug
Indication Solid tumours [ICD11:2D4Z] Preclinical [1]
Structure
3D MOL 2D MOL
Formula
C20H34O5
Canonical SMILES
CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
InChI
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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
InChIKey
PXGPLTODNUVGFL-YNNPMVKQSA-N
CAS Number
CAS 551-11-1
Pharmaceutical Properties Molecular Weight 354.5 Topological Polar Surface Area 98
Heavy Atom Count 25 Rotatable Bond Count 12
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
XLogP
2.7
PubChem CID
5280363
PubChem SID
103214323 ,103943633 ,104046437 ,113853160 ,124892254 ,124892255 ,125307573 ,126662422 ,134340899 ,134978425 ,135651540 ,137006907 ,142063920 ,144205330 ,14852168 ,15398784 ,162205063 ,175268163 ,175607780 ,176484109 ,179116866 ,211534905 ,223673680 ,226412676 ,26754609 ,29216066 ,3912 ,39289529 ,4265953 ,47588758 ,47588759 ,48258963 ,48415906 ,50026801 ,50110092 ,53789218 ,56311306 ,56313004 ,56313208 ,57357710 ,613198 ,77668180 ,7847149 ,7980284 ,8143215 ,8616237 ,92308787 ,92309910 ,99300824 ,99302342
ChEBI ID
CHEBI:15553
TTD Drug ID
D00HTY
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]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [3]
OAT1 Transporter Info Organic anion transporter 1 Substrate [2]
OAT2 Transporter Info Organic anion transporter 2 Substrate [4]
OAT3 Transporter Info Organic anion transporter 3 Substrate [2]
OAT4 Transporter Info Organic anion transporter 4 Substrate [2]
OATP2A1 Transporter Info Organic anion transporting polypeptide 2A1 Substrate [5]
OATP3A1 Transporter Info Organic anion transporting polypeptide 3A1 Substrate [6]
Drug-Transporter Activity Data
Drug-Transporter Activity Data 1-Oct Transporter Info Km =0.477 microM Proximal tubule (S2) cells-OCT1 [2]
2-Oct Transporter Info Km =0.344 microM Proximal tubule (S2) cells-OCT2 [2]
OAT1 Transporter Info Km =0.575 microM Proximal tubule (S2) cells-OAT1 [2]
OAT2 Transporter Info Km =0.425 microM Proximal tubule (S2) cells-OAT2 [4]
OAT3 Transporter Info Km =1.092 microM Proximal tubule (S2) cells-OAT3 [2]
OAT4 Transporter Info Km =0.692 microM Proximal tubule (S2) cells-OAT4 [2]
References
1 Stereocontrolled organocatalytic synthesis of prostaglandin PGF2alpha in seven steps. Nature. 2012 Sep 13;489(7415):278-81.
2 Human organic anion transporters and human organic cation transporters mediate renal transport of prostaglandins. J Pharmacol Exp Ther. 2002 Apr;301(1):293-8.
3 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
4 Interaction of human organic anion transporters 2 and 4 with organic anion transport inhibitors. J Pharmacol Exp Ther. 2002 Jun;301(3):797-802.
5 Cloning, in vitro expression, and tissue distribution of a human prostaglandin transporter cDNA(hPGT). J Clin Invest. 1996 Sep 1;98(5):1142-9.
6 Molecular characterization of human and rat organic anion transporter OATP-D. Am J Physiol Renal Physiol. 2003 Dec;285(6):F1188-97.

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