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Home > Encyclopedia > Isoxsuprine hydrochloride

Isoxsuprine hydrochloride

pharmaceutical raw materials
Isoxsuprine hydrochloride structure

Isoxsuprine hydrochloride 

structure
  • CAS No:

    579-56-6

  • Formula:

    C18H23NO3.ClH

  • Chemical Name:

    Isoxsuprine hydrochloride

  • Synonyms:

    Benzenemethanol,4-hydroxy-α-[1-[(1-methyl-2-phenoxyethyl)amino]ethyl]-,hydrochloride (1:1);Benzyl alcohol,p-hydroxy-α-[1-[(1-methyl-2-phenoxyethyl)amino]ethyl]-,hydrochloride;Benzenemethanol,4-hydroxy-α-[1-[(1-methyl-2-phenoxyethyl)amino]ethyl]-,hydrochloride;Norephedrine,p-hydroxy-N-(1-methyl-2-phenoxyethyl)-,hydrochloride;1-(p-Hydroxyphenyl)-2-(1′-methyl-2′-phenoxy)ethylaminopropanol-1 hydrochloride;Isoxsuprine hydrochloride;Vasodilan;Duvadilan;Isoxsuprin hydrochloride;Dilavase;Navilox;Vasoplex;Isolait;Divadilan;Suprilent;Vasotran;Vadosilan;Duviculine;Suprox SR;Tidilan;34233-88-0;34331-89-0

  • Categories:

    Analytical Chemistry  >  Standard

Description

White Solid


Isoxsuprine hydrochloride is an alkylbenzene.|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.

Isoxsuprine hydrochloride Basic Attributes

337.84

337.14400

209-443-6

DTXSID1045328

Crystals from water|WHITE, CRYSTALLILNE POWDER

2922504500

Characteristics

61.7

4.06410

1.146g/cm3

203-204 °C

484.2ºC at 760mmHg

246.6ºC

INDICES OF REFRACTION; ALPHA 1.508; BETA 1.648; GAMMA 1.670

Soluble in water at 25 deg C, about 2% w/v

2-8°C

LD50 in rats (mg/kg): 1750 orally; 164 i.p. (Goldenthal)

Bitter crystals

172.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

MW: 301.38; mp 102.5-103.5 °C /Isoxsuprine/

Safety Information

UN 3077 9 / PGIII

3

22-50/53-63-50

36-61-60

DO8225000

Xn,N

P301 + P312 + P330

H302-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Aggregated GHS information provided by 47 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Concurrent heavy use /of tobacco smoking/ may interfere with the therapeutic effects of isoxsuprine because nicotine constricts blood vessels.

LD50 Rat oral 1750 mg/kg|LD50 Rat intraperitoneal 164 mg/kg

Drug Information

Adrenergic beta-Agonists; Sympathomimetics; Tocolytic Agents; Vasodilator Agents|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/|Isoxsuprine has been used in the treatment of dysmenorrhea. /NOT included in US product labeling/|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/|For more Therapeutic Uses (Complete) data for ISOXSUPRINE HYDROCHLORIDE (7 total), please visit the HSDB record page.

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

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.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)|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.)|Drugs that selectively bind to and activate beta-adrenergic receptors. (See all compounds classified as Adrenergic beta-Agonists.)

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.

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

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.

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/HUMAN EXPOSURE STUDIES/ The developmental effects of isoxsuprine (I) were assessed in 20 very-low-birth-weight infants whose mothers had received intravenous I within 24 hr of delivery; 40 term and preterm infants served as controls. Infants exposed to I scored significantly lower than the term control group on the Mental Development Index. Neonates born after short term I therapy had outcomes at 2 yr of age similar to those of preterm infants without drug exposure.

Duvadilan

Isoxsuprine hydrochloride Use and Manufacturing

Methods of Manufacturing

P-HYDROXYPROPIOPHENONE IS BENZOYLATED...&...BROMINATED... BROMO COMPD... CONDENSED WITH 1-METHYL-2-PHENOXYETHYLAMINE TO YIELD O-BENZOYLATED PHENONE CORRESPONDING TO ISOXSUPRINE. IN FORM OF ITS HCL, THIS PHENONE IS... DEBENZOYLATED & REDUCED BY HYDROGENATION... ERYTHRO FORM (ISOXSUPRINE)...EXTRACTED... CONVERTED TO HCL

Uses

vasodilator

Dilavase, Duvadilan, Duviculine, Navilox, Suprilent, Vadosilan, Vasolidan, Vasotran|VASODILAN (MEAD JOHNSON). ORAL: TABLETS 10 & 20 MG. INJECTION: SOLN 5 MG/ML IN 2 ML CONTAINERS. TABLET FORM ALSO MARKETED UNDER GENERIC NAME /HYDROCHLORIDE SALT/

Analyte: isoxsuprine hydrochloride; matrix: chemical identification; procedure: ultraviolet absorption spectrophotometry with comparison to standards|Analyte: isoxsuprine hydrochloride; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards|Analyte: isoxsuprine hydrochloride; matrix: pharmaceutical preparation (injection solution); procedure: infrared absorption spectrophotometry with comparison to standards (chemical identification)|Analyte: isoxsuprine hydrochloride; matrix: pharmaceutical preparation (tablet); procedure: infrared absorption spectrophotometry with comparison to standards (chemical identification)|Analyte: isoxsuprine hydrochloride; matrix: pharmaceutical preparation (tablet); procedure: liquid chromatography with detection at 274 nm and comparison to standards (assay purity)

Computed Properties

Molecular Weight:337.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:7
Exact Mass:337.1444713
Monoisotopic Mass:337.1444713
Topological Polar Surface Area:61.7
Heavy Atom Count:23
Complexity:299
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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