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Isoxsuprine Hydrochloride
Also known as: 579-56-6, Duvadilan, Isoxsuprine hcl, Isolait, Dilavase, 4-(1-hydroxy-2-((1-phenoxypropan-2-yl)amino)propyl)phenol hydrochloride
Molecular Formula
C18H24ClNO3
Molecular Weight
337.8  g/mol
InChI Key
QVPSGVSNYPRFAS-UHFFFAOYSA-N

A beta-adrenergic agonist that causes direct relaxation of uterine and vascular smooth muscle. Its vasodilating actions are greater on the arteries supplying skeletal muscle than on those supplying skin. It is used in the treatment of peripheral vascular disease and in premature labor.
1 2D Structure

Isoxsuprine Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[1-hydroxy-2-(1-phenoxypropan-2-ylamino)propyl]phenol;hydrochloride
2.1.2 InChI
InChI=1S/C18H23NO3.ClH/c1-13(12-22-17-6-4-3-5-7-17)19-14(2)18(21)15-8-10-16(20)11-9-15;/h3-11,13-14,18-21H,12H2,1-2H3;1H
2.1.3 InChI Key
QVPSGVSNYPRFAS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(COC1=CC=CC=C1)NC(C)C(C2=CC=C(C=C2)O)O.Cl
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Duvadilan

2. Hydrochloride, Isoxsuprine

3. Isoxsuprine

2.2.2 Depositor-Supplied Synonyms

1. 579-56-6

2. Duvadilan

3. Isoxsuprine Hcl

4. Isolait

5. Dilavase

6. 4-(1-hydroxy-2-((1-phenoxypropan-2-yl)amino)propyl)phenol Hydrochloride

7. Benzenemethanol,4-hydroxy-a-[1-[(1-methyl-2-phenoxyethyl)amino]ethyl]-, Hydrochloride

8. Mls000028704

9. 579-56-6 (hcl)

10. Smr000058729

11. Vadosilan

12. Dsstox_cid_25328

13. Dsstox_rid_80806

14. Dsstox_gsid_45328

15. Duviculine

16. Navilox

17. 34331-89-0

18. Nsc-757067

19. Duvadilan (tn)

20. Prestwick_500

21. Opera_id_1429

22. Ncgc00016512-01

23. Cas-579-56-6

24. Mls001148084

25. Mls002695887

26. Schembl124661

27. Chembl559180

28. Dtxsid1045328

29. Chebi:31735

30. Hms1568m17

31. Hy-b1270

32. Tox21_110467

33. 4-[1-hydroxy-2-(1-phenoxypropan-2-ylamino)propyl]phenol;hydrochloride

34. S5669

35. Akos030254697

36. Isoxsuprine Hydrochloride (jp17/usp)

37. Tox21_110467_1

38. Ccg-220068

39. Cs-8212

40. Nc00514

41. Ncgc00018295-05

42. Ncgc00094704-01

43. Ncgc00094704-02

44. Ncgc00094704-03

45. As-76145

46. Db-053134

47. Ft-0603478

48. Isoxsuprine Hydrochloride, Analytical Standard

49. D01748

50. D81952

51. Sr-01000000272

52. Sr-01000000272-2

53. Erythro-isoxsuprine Hydrochloride, Vetranal(tm), Analytical Standard

54. 4-(1-hydroxy-2-((1-phenoxypropan-2-yl)amino)propyl)phenolhydrochloride

55. 4-(1-hydroxy-2-(1-phenoxypropan-2-ylamino)propyl)phenol Hydrochloride

56. 5-methyl-2-phenyl-2,5-dihydro-1h-pyrazol-3-yl2-chloronicotinate

57. Isoxsuprine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

58. Isoxsuprine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

2.2.3 Other Synonyms

1. Dilavase

2. Vasodilian

3. Vasosurpine

4. Isoxuprine

2.3 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 337.8 g/mol
Molecular Formula C18H24ClNO3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass337.1444713 g/mol
Monoisotopic Mass337.1444713 g/mol
Topological Polar Surface Area61.7 Ų
Heavy Atom Count23
Formal Charge0
Complexity299
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count3
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Adrenergic beta-Agonists; Sympathomimetics; Tocolytic Agents; Vasodilator Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Isoxsuprine is also used for management of threatened premature labor in pregnancies of 20 or more weeks' gestation. Use in not recommended prior to the 20th week of pregnancy. For isoxsuprine to be most effective, it is recommended that therapy be started as soon as the diagnosis of preterm labor is confirmed. Efficacy in advanced labor has not been established. Use in patients with ruptured membranes must be weighed against the risk of intrauterine infection. /NOT included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc.


Isoxsuprine has been used in the treatment of dysmenorrhea. /NOT included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc.


FDA has classified isoxsuprine as being possibly effective for its labeled indications, which include relief of symptoms associated with cerebrovascular insufficiency and peripheral vascular disease, ie, arteriosclerosis obliterans, thromboangiitis obliterans (Buerger's disease), and Raynaud's disease. This classification requires the submission of adequate and well-controlled studies in order to provide substantial evidence of effectiveness. /Included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc.


For more Therapeutic Uses (Complete) data for ISOXSUPRINE HYDROCHLORIDE (7 total), please visit the HSDB record page.


4.2 Drug Warning

Except under special circumstances, this medication /isoxsuprine hydrochloride/ should not be used immediately postpartum or when the following medical problems exist: For use in management of premature labor only: Cardiac disorders, especially those associated with arrhythmias, or maternal hyperthyroidism (isoxsuprine may precipitate arrhythmias or heart failure; occult cardiac disease may be unmasked) or chorioamnionitis (intrauterine infection) or hemorrhage or intrauterine fetal death or known abnormality (immediate delivery required) or eclampsia (toxemia) and severe pre-eclampsia or pulmonary hypertension.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc.


Isoxsuprine has both beta-1 and beta-2 adrenergic activity. Maternal hypotension and tachycardia are common side effects. Hypocalcemia, hypoglycemia, hypotension, ileus, and neonatal death are increased after isoxsuprine administration.

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 163


...When injected sc in human beings causes several mm of mercury transient elevation of ocular pressure, max in an hr or two, associated with edema and hyperemia of episcleral tissues.

Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 612


Adverse effects of isoxsuprine include trembling, nervousness, weakness, dizziness, flushing, transient palpitation, tachycardia, chest pain, hypotension, abdominal distress, nausea, vomiting, intestinal distention, and severe rash.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1707


For more Drug Warnings (Complete) data for ISOXSUPRINE HYDROCHLORIDE (8 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 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.)


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.)


Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


Adrenergic beta-Agonists

Drugs that selectively bind to and activate beta-adrenergic receptors. (See all compounds classified as Adrenergic beta-Agonists.)


5.2 Absorption, Distribution and Excretion

Isoxsuprine hydrochloride is almost completely absorbed from the gastrointestinal tract. After oral admin of the drug, peak plasma concns occur within 1 hr and persist for about 3 hr. ...Isoxsurprine crosses the placenta. The drug is partially conjugated in the body and is excreted in the urine. Fecal excretion of the drug is negligible.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1707


5.3 Biological Half-Life

Mean plasma half-life of the drug is 1.25 hr.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1707


5.4 Mechanism of Action

Isoxsuprine produces peripheral vasodilation by a direct effect on vascular smooth muscle, primarily within skeletal muscle with little effect on cutaneous blood flow. Its effects were once thought to be due to beta-adrenergic receptor stimulation but are not reversed by beta-adrenergic blocking agents.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 23rd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2003. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc.


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