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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H30N2O2.ClH
Molecular Weight 414.968
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXAPRAM HYDROCHLORIDE, (R)-

SMILES

Cl.CCN1C[C@H](CCN2CCOCC2)C(C1=O)(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=MBGXILHMHYLZJT-FTBISJDPSA-N
InChI=1S/C24H30N2O2.ClH/c1-2-26-19-22(13-14-25-15-17-28-18-16-25)24(23(26)27,20-9-5-3-6-10-20)21-11-7-4-8-12-21;/h3-12,22H,2,13-19H2,1H3;1H/t22-;/m0./s1

HIDE SMILES / InChI
Doxapram is racemic and exists as a racemate with positive ( ) and negative (−) enantiomers. The respiratory stimulant properties of doxapram would be stereoselective and could be evaluated by chirally separating doxapram into its ( ) enantiomer (GAL-054) and (−) enantiomer (GAL-053). Pre-clinically we demonstrated that the ( ) enantiomer, GAL-054, and not the (−) enantiomer, GAL-053, dose-dependently increased minute volume when administered intravenously to drug naïve and opioid challenged rats and cynomolgus monkeys. Moreover, the deleterious side-effects of agitation and seizures were restricted to GAL-053. There were minimal behavioral changes observed in rats and monkeys receiving GAL-054. Thus, GAL-054 is the eutomer and GAL-053 the distomer of doxapram. Unfortunately, in conscious rats GAL-054 increased blood pressure approximately 15–20% above baseline values at doses that were moderately respiratory stimulant. This effect was confirmed in a Phase 1 clinical trial evaluating the effects of GAL-054 in healthy volunteers (Galleon Pharmaceuticals, unpublished data). Thus, the ventilatory stimulant and pressor effects of doxapram cannot be separated by enantiomeric separation of the racemate.

Approval Year

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vitro Use Guide
Unknown
Name Type Language
DOXAPRAM HYDROCHLORIDE, (R)-
Common Name English
2-PYRROLIDINONE, 1-ETHYL-4-(2-(4-MORPHOLINYL)ETHYL)-3,3-DIPHENYL-, HYDROCHLORIDE (1:1), (4R)-
Systematic Name English
Code System Code Type Description
FDA UNII
97Q6519W0N
Created by admin on Sat Dec 16 11:26:38 GMT 2023 , Edited by admin on Sat Dec 16 11:26:38 GMT 2023
PRIMARY
PUBCHEM
71569329
Created by admin on Sat Dec 16 11:26:38 GMT 2023 , Edited by admin on Sat Dec 16 11:26:38 GMT 2023
PRIMARY
CAS
1432475-05-2
Created by admin on Sat Dec 16 11:26:38 GMT 2023 , Edited by admin on Sat Dec 16 11:26:38 GMT 2023
PRIMARY