Dobutamine

Title: Dobutamine
CAS Registry Number: 34368-04-2
CAS Name: 4-[2-[[3-(4-Hydroxyphenyl)-1-methylpropyl]amino]ethyl]-1,2-benzenediol
Additional Names: (±)-4-[2-[[3-(p-hydroxyphenyl)-1-methylpropyl]amino]ethyl]pyrocatechol; 3,4-dihydroxy-N-[3-(4-hydroxyphenyl)-1-methylpropyl]-b-phenylethylamine
Manufacturers' Codes: Compound 81929
Molecular Formula: C18H23NO3
Molecular Weight: 301.38
Percent Composition: C 71.73%, H 7.69%, N 4.65%, O 15.93%
Literature References: b1-Adrenergic agonist; derivative of dopamine, q.v. Prepn: R. R. Tuttle, J. Mills, DE 2317710; eidem, US 3987200 (1973, 1976 to Lilly). Pharmacology: R. Weber, R. R. Tuttle in Pharmacological and Biochemical Properties of Drug Substances vol. 1, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1977) pp 109-124; E. H. Sonnenblick et al., N. Engl. J. Med. 300, 17 (1979). Comprehensive description: R. H. Bishara, H. B. Long, Anal. Profiles Drug Subs. 8, 139-158 (1979).
Derivative Type: Hydrochloride
CAS Registry Number: 49745-95-1
Trademarks: Inotrex (obsolete) (Lilly); Dobutrex (Lilly)
Molecular Formula: C18H23NO3.HCl
Molecular Weight: 337.84
Percent Composition: C 63.99%, H 7.16%, N 4.15%, O 14.21%, Cl 10.49%
Properties: Crystals, mp 184-186°. uv max (methanol): 281, 223 nm (e 4768, 14400). pKa 9.45. Rapidly oxidized at pH 11-13. LD50 i.v. in mice: ~73 mg/kg (Weber, Tuttle).
Melting point: mp 184-186°
pKa: pKa 9.45
Absorption maximum: uv max (methanol): 281, 223 nm (e 4768, 14400)
Toxicity data: LD50 i.v. in mice: ~73 mg/kg (Weber, Tuttle)
Therap-Cat: Cardiotonic.
Keywords: Cardiotonic.
Docarpamine Docetaxel Docosahexaenoic Acid Docusate Calcium Docusate Sodium

Dobutamine
Dobutamine skeletal.svg
Systematic (IUPAC) name
(RS)-4-(2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)benzene-1,2-diol
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682861
Pregnancy cat. B
Legal status Prescription only
Routes Intravenous
Pharmacokinetic data
Half-life 2 minutes
Identifiers
CAS number 34368-04-2 YesY
ATC code C01CA07
PubChem CID 36811
IUPHAR ligand 535
DrugBank DB00841
ChemSpider 33786 YesY
UNII 0WR771DJXV YesY
KEGG D03879 YesY
ChEBI CHEBI:4670 YesY
ChEMBL CHEMBL926 YesY
Synonyms Dobutrex, Inotrex
Chemical data
Formula C18H23NO3 
Mol. mass 301.38 g/mol
 YesY (what is this?)  (verify)

Dobutamine is a sympathomimetic drug used in the treatment of heart failure and cardiogenic shock. Its primary mechanism is direct stimulation of β1 receptors of the sympathetic nervous system. Dobutamine was developed in the 1970s by Drs. Ronald Tuttle and Jack Mills at Eli Lilly and Company, as a structural analogue of isoprenaline.[1]