Responsive image

Common name


Treprostinil

IUPAC name


2-{[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid

SMILES


[H][C@]12C[C@@H](O)[C@H](CC[C@@H](O)CCCCC)[C@@]1([H])CC1=C(C2)C(OCC(O)=O)=CC=C1

Compound class


Antithrombins; Anticoagulants; Antihypertensive Agents; Antithrombotic Agents; Blood and Blood Forming Organs; Platelet Aggregation Inhibitors Excl. Heparin; Cytochrome P-450 CYP2C9 Inhibitors; Cytochrome P-450 CYP2C9 Inducers;

Therapeutic area


For use as a continuous subcutaneous infusion or intravenous infusion (for those not able to tolerate a subcutaneous infusion) for the treatment of pulmonary arterial hypertension in patients with NYHA Class II-IV symptoms to diminish symptoms associated with exercise.

Common name


Treprostinil

IUPAC name


2-{[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid

SMILES


[H][C@]12C[C@@H](O)[C@H](CC[C@@H](O)CCCCC)[C@@]1([H])CC1=C(C2)C(OCC(O)=O)=CC=C1

INCHI


InChI=1S/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m0/s1

FORMULA


C23H34O5

Responsive image

Common name


Treprostinil

IUPAC name


2-{[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid

Molecular weight


390.513

clogP


4.087

clogS


-4.123

HBond Acceptor


5

HBond Donor


3

Total Polar
Surface Area


86.99

Number of Rings


3

Rotatable Bond


10

Drug ID Common name Structure CAS SMILE Frequency
FDBF00004 acetic acid Responsive image CC(=O)O 0.0687
FDBF00007 propane Responsive image C(C)C 0.2412
FDBF00018 propan-1-ol Responsive image C(O)CC 0.0330
FDBF00041 ethanol Responsive image CCO 0.1474
FDBF00067 butane Responsive image CCCC 0.0680
FDBF00406 (2R)-butan-2-ol Responsive image CCC(C)O 0.0055
FDBF00441 (2R)-pentan-2-ol Responsive image C(CC)C(C)O 0.0010
FDBF00819 (1R,2R,3aS,9aS)-1-methyl-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-2-ol Responsive image C12C(CC(C1C)O)Cc3c(cccc3)C2 0.0003
FDBF00820 (1R,2R,3aS,9aS)-1-methyl-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[g]naphthalene-2,5-diol Responsive image Oc1c2c(ccc1)CC3C(C2)CC(C3C)O 0.0003
FDBF00823 (3R)-hexan-3-ol Responsive image CCC(O)CCC 0.0003
20 , 3