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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28N2O3
Molecular Weight 368.4693
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTAMORPHONE

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]15CCN(C)[C@H](C4)[C@]5(NCCCCC)C=CC2=O

InChI

InChIKey=NRPCWSUJMWEFOK-KDXIVRHGSA-N
InChI=1S/C22H28N2O3/c1-3-4-5-11-23-22-9-8-16(26)20-21(22)10-12-24(2)17(22)13-14-6-7-15(25)19(27-20)18(14)21/h6-9,17,20,23,25H,3-5,10-13H2,1-2H3/t17-,20+,21+,22-/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H28N2O3
Molecular Weight 368.4693
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Pentamorphone was developed as a highly potent opioid with rapid onset and short duration of action that has been reported to produce analgesia with limited depression of ventilation. Pentamorphone participated in a clinical trial for the management of postoperative pain. However, no acute cardiorespiratory changes were observed. The drug was ineffective for treating acute postoperative pain after major surgery. In addition, was shown that pentamorphone, 10 micrograms/kg, does not seem to offer any significant advantage over opioids currently used for anesthesia in patients undergoing elective coronary artery bypass grafting (CABG). That is why its further development was discontinued.

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
double-blind study of 72 patients given 0.08, 0.16, or 0.24 micrograms/kg of pentamorphone or a placebo intravenously in the recovery room after major abdominal or orthopedic surgery.
Route of Administration: Intravenous
Substance Class Chemical
Record UNII
MM4487B4MW
Record Status Validated (UNII)
Record Version