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Prestwick3_000349

Prestwick3_000349

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Also known as: Ritodrina [inn-spanish], Ritodrinium [inn-latin], 26652-09-5, Du-21220, Prepar, P-hydroxy-alpha-(1-((p-hydroxyphenethyl)amino)ethyl)benzyl alcohol

Molecular Formula

C₁₇H₂₁NO₃

Molecular Weight

287.35 g/mol

InChI Key

IOVGROKTTNBUGK-SJCJKPOMSA-N

An adrenergic beta-2 agonist used to control PREMATURE LABOR.

1 2D Structure

Prestwick3_000349

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[2-[[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenol

2.1.2 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

2.1.3 InChI Key

IOVGROKTTNBUGK-SJCJKPOMSA-N

2.1.4 Canonical SMILES

CC(C(C1=CC=C(C=C1)O)O)NCCC2=CC=C(C=C2)O

2.1.5 Isomeric SMILES

C[C@@H]([C@@H](C1=CC=C(C=C1)O)O)NCCC2=CC=C(C=C2)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Du 21220

2. Du-21220

3. Du21220

4. Hydrochloride, Ritodrine

5. Pre Par

6. Pre-par

7. Prepar

8. Ritodrine Hydrochloride

9. Yutopar

2.2.2 Depositor-Supplied Synonyms

1. Ritodrina [inn-spanish]

2. Ritodrinium [inn-latin]

3. 26652-09-5

4. Du-21220

5. Prepar

6. P-hydroxy-alpha-(1-((p-hydroxyphenethyl)amino)ethyl)benzyl Alcohol

7. Mls002153782

8. Ritodrine (usan/inn)

9. Smr001233166

10. (?)-ritodrine

11. Prestwick0_000349

12. Prestwick1_000349

13. Prestwick2_000349

14. Prestwick3_000349

15. Chembl785

16. 4-[(1r,2s)-1-hydroxy-2-{[2-(4-hydroxyphenyl)ethyl]amino}propyl]phenol

17. Schembl34194

18. Bspbio_000417

19. Cid_31728

20. Spbio_002338

21. Bpbio1_000459

22. Chebi:8872

23. Gtpl7294

24. Dtxsid7048534

25. Bdbm97162

26. Zinc57480

27. Db00867

28. Ncgc00179566-01

29. Ncgc00179566-03

30. C07239

31. D02359

32. Q5577596

33. Brd-k51465424-003-03-6

34. 4-(2-{[(1r,2s)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino}ethyl)phenol

2.3 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₁NO₃
Molecular Weight	287.35 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	287.15214353 g/mol
Monoisotopic Mass	287.15214353 g/mol
Topological Polar Surface Area	72.7 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	284
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment and prophylaxis of premature labour

5 Pharmacology and Biochemistry

5.1 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.

5.2 MeSH Pharmacological Classification

Sympathomimetics

Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)

Adrenergic beta-2 Receptor Agonists

Compounds bind to and activate ADRENERGIC BETA-2 RECEPTORS. (See all compounds classified as Adrenergic beta-2 Receptor Agonists.)

Tocolytic Agents

Drugs that prevent preterm labor and immature birth by suppressing uterine contractions (TOCOLYSIS). Agents used to delay premature uterine activity include magnesium sulfate, beta-mimetics, oxytocin antagonists, calcium channel inhibitors, and adrenergic beta-receptor agonists. The use of intravenous alcohol as a tocolytic is now obsolete. (See all compounds classified as Tocolytic Agents.)

5.3 ATC Code

G - Genito urinary system and sex hormones

G02 - Other gynecologicals

G02C - Other gynecologicals

G02CA - Sympathomimetics, labour repressants

G02CA01 - Ritodrine

5.4 Metabolism/Metabolites

Hepatic, by both the mother and fetus

5.5 Biological Half-Life

1.7-2.6 hours

5.6 Mechanism of Action

Ritodrine is beta-2 adrenergic agonist. It binds to beta-2 adrenergic receptors on outer membrane of myometrial cell, activates adenyl cyclase to increase the level of cAMP which decreases intracellular calcium and leads to a decrease of uterine contractions.