4-[(1R,2S)-1-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]amino}propyl]phenol

• ChemBase ID: 745
• Molecular Formular: C17H21NO3
• Molecular Mass: 287.35354
• Monoisotopic Mass: 287.15214354
• SMILES: O[C@@H]([C@@H](NCCc1ccc(O)cc1)C)c1ccc(O)cc1
• Canonical SMILES: Oc1ccc(cc1)CCN[C@H]([C@@H](c1ccc(cc1)O)O)C
• InChI: InChI=1S/C17H21NO3/c1-12(17(21)14-4-8-16(20)9-5-14)18-11-10-13-2-6-15(19)7-3-13/h2-9,12,17-21H,10-11H2,1H3/t12-,17-/m0/s1
• InChIKey: IOVGROKTTNBUGK-SJCJKPOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R,2S)-1-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]amino}propyl]phenol
• IUPAC Traditional name: 4-[(1R,2S)-1-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]amino}propyl]phenol
• Brand Name: Yutopar; Yutopar S.R
• Synonyms: Ritodrina [INN-Spanish]; Ritodrine Hcl; Ritodrine Hydrochloride; Ritodrinium [INN-Latin]; Ritodrine

Database IDs

• CAS Number: 26652-09-5
• PubChem SID: 160964208; 46505273
• PubChem CID: 33572

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.154391
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.4678472
• LogD (pH = 7.4): 0.5068871
• Log P: 1.8155849
• Molar Refractivity: 83.0167 cm^3
• Polarizability: 32.40149 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.53
• LOG S: -3.21
• Solubility (Water): 1.79e-01 g/l

PROPERTIES

Physical Property

• Solubility: Complete
• Hydrophobicity(logP): 2.4

DETAILS

DrugBank - DB00867

• Drug Groups: approved
• Description: Adrenergic beta-agonist used to control premature labor. [PubChem]
• Indication: For the treatment and prophylaxis of premature labour
• Pharmacology: Beta-2 adrenergic receptors are located at sympathetic neuroeffector junctions of many organs, including uterus. Ritodrine is beta-2 adrenergic agonist. It stimulates beta-2 adrenergic receptor, increases cAMP level and decreases intracellular calcium concentration. The decrease of calcium concentration leads to a relaxation of uterine smooth muscle and, therefore, a decrease in premature uterine contractions.
• Toxicity: LD₅₀=64mg/kg (mice, IV); LD₅₀=540 mg/kg (mice, oral); LD₅₀=85 mg/kg (rat, IV)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, by both the mother and fetus
• Half Life: 1.7-2.6 hours
• Protein Binding: ~56%
• External Links: Wikipedia; Drugs.com