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Alverine

Alverine structure

CAS No:
150-59-4
Formula:
C20H27N
Chemical Name:
Alverine
Synonyms:
Benzenepropanamine,N-ethyl-N-(3-phenylpropyl)-;Dipropylamine,N-ethyl-3,3′-diphenyl-;N-Ethyl-N-(3-phenylpropyl)benzenepropanamine;Alverine;Bis(γ-phenylpropyl)ethylamine;Dipropylin;Dipropyline;Phenopropamine;Profenil;Sestron;Sestron base;Phenpropamine
Categories:
Organic Chemistry > Amides

Description

ChEBI: A tertiary amine having one ethyl and two 3-phenylprop-1-yl groups attached to the nitrogen. An antispasmodic that acts directly on intestinal and uterine smooth muscle, it is used (particularly as the citrate salt) in the treatment of irritable bowel synd ome.

Solid

Alverine is a tertiary amine having one ethyl and two 3-phenylprop-1-yl groups attached to the nitrogen. An antispasmodic that acts directly on intestinal and uterine smooth muscle, it is used (particularly as the citrate salt) in the treatment of irritable bowel syndrome. It has a role as an antispasmodic drug. It is a conjugate base of an alverine(1+).|Alverine is a smooth muscle relaxant used to relieve cramps or spasms of the stomach and intestines. It is therefore useful in treating irritable bowel syndrome (IBS) and similar conditions. It can also be used to help relieve period pain.

Alverine Basic Attributes

Molecular Weight：

281.44

Exact Mass：

281.44

EC Number：

205-763-5

UNII：

46TIR1560O

DSSTox ID：

DTXSID0048557

Color/Form：

LIQUID

ATC Code：

A03AX08|A - Alimentary tract and metabolism

HScode：

2921499090

Characteristics

PSA：

3.2

XLogP3：

5.93

Appearance：

Solid

Density：

0.973±0.06 g/cm3(Predicted)

Melting Point：

<25 °C

Boiling Point：

165-168 °C @ Press: 0.3 Torr

Flash Point：

174.4±21.7 °C

Refractive Index：

1.548

Water Solubility：

9.60e-04 g/L

Experimental Properties：

10% AQ SOLN IS NEUTRAL TO LITMUS /CITRATE/

Safety Information

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501

Hazard Statements：

H302

Toxicity

Toxicity Summary：

Can produce hypotension and atropine-like toxic effects. Fatality has occurred following overdose with very high doses.

Drug Information

Drug Indication：

Used to relieve cramps or spasms of the stomach and intestines. It is also useful in treating irritable bowel syndrome (IBS) and similar conditions. It can also be used to help relieve period pain. Alverine citrate is also under investigation to increase the cytotoxic effects of the proteasome inhibitor MG132 on breast cancer cells.

Therapeutic Uses：

Parasympatholytics|IT IS USED IN MGMNT OF GI DISORDERS IN WHICH HYPERMOTILITY OR SPASM IS INVOLVED...& IN GENITOURINARY SPASM SUCH AS MAY ACCOMPANY PASSAGE OF STONE, URINARY TRACT INFECTION, OR PROSTATIC HYPERTROPHY. ... IT MAY ALSO BE USED IN CERTAIN PRIMARY DYSMENORRHEAS & TO AID IN VARIOUS ENDOSCOPIC EXAM. /CITRATE/|STERCULIA GUM WITH & WITHOUT SMOOTH MUSCLE RELAXANT ALVERINE HAD SIMILAR BENEFICIAL EFFECTS ON CONSTIPATION & REDUCED TRANSIT TIMES IN DIVERTICULAR DISEASE IN 2 GROUPS OF 10 PT STUDIED.|ANTICHOLINERGIC

Drug Warnings：

IT PROBABLY SHOULD BE USED WITH CAUSTION IN AGED & ARTERIOSCLEROTIC PT & IN PRESENCE OF ANGINA PECTORIS. /CITRATE/

Pharmacology：

Alverine is a smooth muscle relaxant. Smooth muscle is a type of muscle that is not under voluntary control; it is the muscle present in places such as the gut and uterus. Alverine acts directly on the muscle in the gut, causing it to relax. This prevents the muscle spasms which occur in the gut in conditions such as irritable bowel syndrome and diverticular disease. Diverticular disease is a condition in which small pouches form in the gut lining. These pouches can trap particles of food and become inflamed and painful. In irritable bowel syndrome the normal activity of the gut muscle is lost. The muscle spasms result in symptoms such as heartburn, abdominal pain and bloating, constipation or diarrhoea. By relaxing the gut muscle, alverine citrate relieves the symptoms of this condition. Alverine also relaxes the smooth muscle in the womb (uterus). It is therefore also used to treat painful menstruation, which is caused by muscle spasms in the uterus (dysmenorrhea).

MeSH：

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)

Absorption：

High renal clearance of all metabolites indicating that they are eliminated by active renal secretion.

Metabolism/Metabolites：

Rapidly converted to its primary active metabolite, which is then further converted to two secondary metabolites.

Biological Half-Life：

The plasma half-life averages 0.8 hours for alverine and 5.7 hours for the active primary metabolite.

MeSH Entry Terms：

alverine

Alverine Use and Manufacturing

Methods of Manufacturing

PREPD FROM PHENYLPROPYL CHLORIDE & ETHYLAMINE IN ALKALINE MEDIUM: KULZ ET AL, BER 72, 2165 (1939); ALTERNATE ROUTE: STUHNER, ELBRACHTER, ARCH PHARM 287, 139 (1954).

Uses

Anticholinergic.

Formulations：

ANTISPASMIN, CALMABEL, GAMATRAN, PROFENIL, PROFENINE, PROPHELAN, PROVERINE SESTRON, SPACOLIN, SPASMAVERINE. /CITRATE/

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:281.4
XLogP3:5.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:9
Exact Mass:281.214349865
Monoisotopic Mass:281.214349865
Topological Polar Surface Area:3.2
Heavy Atom Count:21
Complexity:214
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes