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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H23N5O3
Molecular Weight 357.4069
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAFEDRINE

SMILES

C[C@H](NCCN1C=NC2=C1C(=O)N(C)C(=O)N2C)[C@H](O)C3=CC=CC=C3

InChI

InChIKey=UJSKUDDDPKGBJY-WFASDCNBSA-N
InChI=1S/C18H23N5O3/c1-12(15(24)13-7-5-4-6-8-13)19-9-10-23-11-20-16-14(23)17(25)22(3)18(26)21(16)2/h4-8,11-12,15,19,24H,9-10H2,1-3H3/t12-,15-/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H23N5O3
Molecular Weight 357.4069
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cafedrine, also known as norephedrinoethyltheophylline, is a chemical linkage of norephedrine and theophylline and is a cardiac stimulant used to increase blood pressure in people with hypotension. There are few data available for cafedrine. Cafedrine has a half-life of 60 min following both oral and intravenous administration Cafedrine is metabolized to norephedrine and several minor metabolites, but nearly 90% of the administered norephedrine is excreted via the kidneys, mostly unchanged, within 24 h. The effects of cafedrine on cardiac output are believed to be mediated via β- adrenoceptors. Cafedrine has a positive inotropic effect in humans, and this can be abolished by administration of the non-selective β-adrenoceptor antagonist propranolol. A combination of cafedrine and theodrenaline called Akrinor® is used for the treatment of hypotension in adults that occurs during emergency situations, general anesthesia, and regional anesthesia, especially during cesarean sections. Cafedrine/theodrenaline may have advantages over other vasopressor drugs. For example, it can be administered via bolus while catecholamines normally need to be diluted and administered via syringe pumps. Bolus injection is faster, which may be beneficial in emergency situations, plus it is more cost efficient with respect to the disposables. Cafedrine/theodrenaline has been widely used in Germany since 1963

Approval Year

PubMed

Patents

Substance Class Chemical
Record UNII
0UYY5V4U2Q
Record Status Validated (UNII)
Record Version