Propantheline
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Propantheline
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CAS No:
298-50-0
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Formula:
C23H30NO3
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Chemical Name:
Propantheline
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Synonyms:
2-Propanaminium,N-methyl-N-(1-methylethyl)-N-[2-[(9H-xanthen-9-ylcarbonyl)oxy]ethyl]-;Ammonium,(2-hydroxyethyl)diisopropylmethyl-,xanthene-9-carboxylate (ester);N-Methyl-N-(1-methylethyl)-N-[2-[(9H-xanthen-9-ylcarbonyl)oxy]ethyl]-2-propanaminium;Propantheline;Propanthelinium
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CAS No:
Description
Solid
Solid
Propantheline is a member of xanthenes.|A muscarinic antagonist used as an antispasmodic, in rhinitis, in urinary incontinence, and in the treatment of ulcers. At high doses it has nicotinic effects resulting in neuromuscular blocking.|Propantheline is an Anticholinergic. The mechanism of action of propantheline is as a Cholinergic Antagonist.|Propantheline is an anticholinergic agent used to treat gastrointestinal conditions associated with intestinal spasm and to decrease secretions during anesthesia. Propantheline has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.
Propantheline Basic Attributes
294.39
294.19400
206-063-2
1306V2B0Q8
DTXSID6047230
A - Alimentary tract and metabolism
Characteristics
64.79000
3.13740
Solid
7.22e-05 g/L
Crystals from isopropanol plus ether; very soluble in water, alcohol, chloroform; practically insol in ether, benzene; mp: 159-161 °C /Bromide/|WHITE OR NEARLY WHITE CRYSTALS; ODORLESS & HAS BITTER TASTE; MELTS BETWEEN 156 & 162 °C WITH DECOMP /BROMIDE/
Safety Information
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
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).
Toxicity
Like other anticholinergic agents, propantheline has not been linked to episodes of liver enzyme elevations or clinically apparent liver injury. It is metabolized at least partially in the liver. A reason for its safety may relate to the low daily dose.
GI ABSORPTION OF PROPANTHELINE IS INCR BY SODIUM BICARBONATE...|RATE & EXTENT OF ABSORPTION OF.../ORALLY/ DOSED PARACETAMOL IS REDUCED BY...PROPANTHELINE...|CONCURRENT USE OF PROPANTHELINE WITH SLOW-DISSOLVING TABLETS OF DIGOXIN MAY CAUSE INCR SERUM DIGOXIN LEVELS. THIS INTERACTION CAN BE AVOIDED BY USING ONLY THOSE DIGOXIN TABLETS THAT ARE FAST DISSOLVING BY USP STD.|.../TREATMENT WITH/ PROPANTHELINE, INCR /GI/ ABSORPTION /OF PHENOLSULFOPHTHALEIN IN MAN/ UP TO 24% OWING TO DECR GI TRANSIT RATE.|For more Interactions (Complete) data for PROPANTHELINE (14 total), please visit the HSDB record page.
Propantheline bromide (PB) ... was tested for its effects on reproduction & fertility in CD-1 mice using the RACB protocol. Data on food & water consumption, body weights, & clinical signs during a 2 wk dose-range-finding study (Task 1) were used to set exposure concns for the Task 2 continuous cohabitation study at 0.0, 0.05, 0.16, & 0.5% in feed. Based on mean body weight & avg feed consumption data, the estimated daily doses were 71, 235, & 760 mg/kg bw. In the F0 animals, there were no deaths during Task 2. Body weight gain for the top dose males was reduced by a factor of 4, compared to controls. There was a statistically significant, but small (6%) reduction in the number of litters/pair at the top dose. The only other changes in reproductive indices for the F0 pairs occurred at the high dose level, & were a reduction in the mean weight of F1 pups adjusted for litter size at the top dose, by 4%, & an incr in the length of time to deliver each litter. This delay was greatest for the first 3 litters, while the difference was less for the last 2 litters. These modest reproductive effects (6% decr in litters/pair, & 4% decr in adjusted live pup weight) were considered too small to be detectable in the single litter generated by the Task 3 crossover, so Task 3 was not conducted. There were no adverse effects of PB consumption on the growth or viability of the F1 offspring in the last litter that was reared for second generation testing. After weaning the F2 mice, the F1 mice from control, middle & high dose groups were killed & necropsied. There were no weight changes or gross lesions noted in females, while male body weights were reduced by 11% at the top dose. There were no changes in sperm indices or in estrous cycle parameters. Only mice from the control & high dose groups were kept & treated with PB from weaning to the mating trial at /postnatal day/ 74 +/- 10. Compared to controls, the high dose PB mice had similar-sized litters, with the same proportion of live pups, & same sex ratio, but the adjusted live pup weight was reduced by 11%. After the delivery & evaluation of the F2 litters & estrous cycle data collection, the F1 adults were killed & necropsied. There was an 8% reduction in female body weight, & no change in organ weights. For males, body weight was reduced by 10%, & prostate weight was reduced by 25%. Epididymal sperm density was reduced at the high dose by 15%, while estrous cycle length & characteristics were unchanged. Thus, propantheline bromide caused detectable but small reductions in litter number, in both generations reduced adjusted pup weight, & reduced F1 prostate weight & sperm count. These effects were seen concomitant with male body weight changes but no other significant non-reproductive toxicities. /Propantheline bromide/
Drug Information
For the treatment of enuresis. It has also been used for hyperhidrosis, and cramps or spasms of the stomach, intestines or bladder.
Propantheline is an anticholinergic agent used to treat gastrointestinal conditions associated with intestinal spasm and to decrease secretions during anesthesia. Propantheline has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.
Anticholinergic Agents
Anti-Ulcer Agents; Muscarinic Antagonists; Parasympatholytics|ANTICHOLINERGIC AGENTS (EG ... PROPANTHELINE) ... /IS USED FOR/ ANTISPASMODIC EFFECTS TO TREAT HYPERTONICITY & UNCONTROLLED CONTRACTION OF URINARY BLADDER & TO REDUCE SYMPTOMS OF DYSURIA & URINARY URGENCY & FREQUENCY ASSOC WITH ... NEUROGENIC BLADDER, CYSTITIS, PROSTATITIS, OR URETHRITIS.|BENEFICIAL EFFECTS IN PEPTIC ULCER MOSTLY DERIVED FROM DECR GASTRIC MOTILITY, ALTHOUGH SOME SUPPRESSION OF GASTRIC SECRETION OCCURS AFTER PARENTERAL ADMIN. /PROPANTHELINE BROMIDE/|MEDICATION (VET): /USE AS/ GI SEDATIVE... /BROMIDE/|For more Therapeutic Uses (Complete) data for PROPANTHELINE (9 total), please visit the HSDB record page.
...PRACTITIONER SHOULD BE ALERT FOR SIGNS OF DIGITALIS TOXICITY IN ANY PT RECEIVING DIGOXIN TABLETS & PROPANTHELINE CONCURRENTLY. ... OTHER DRUGS RELATED TO DIGOXIN INCL ACETYLDIGITOXIN DESLANOSIDE, DIGITALIS, GITALIN, LANATOSIDE C & OUABAIN.|There are no clinically significant, clear-cut differences in efficacy among the anticholinergic antispasmodics to aid in drug selection, and, ... no available anticholinergic drug has a particular advantage over others. /Anticholinergic drugs/|In 1 series of patients oral doses of 75 mg/day caused subjective difficulty with vision in only 4/69, presumably from interference with accomodation. In another series 120 mg given orally to 16 normal people 20-35 yr of age had no effect on near point of accomodation. /Propantheline bromide/|...During test period /in tests relating to glaucoma, tension/ rose in 3 chronic simple openangle glaucomatous eyes, in 1 with "chronic congestive", & in 1 with "secondary" glaucoma. Without /adequate/ information ... it is uncertain whether drug was responsible for these tension elevations.|For more Drug Warnings (Complete) data for PROPANTHELINE (9 total), please visit the HSDB record page.
Propantheline is an anticholinergic drug, a medication that reduces the effect of acetylcholine, a chemical released from nerves that stimulates muscles, by blocking the receptors for acetylcholine on smooth muscle (a type of muscle). It also has a direct relaxing effect on smooth muscle. Propantheline is used to treat or prevent spasm in the muscles of the gastrointestinal tract in the irritable bowel syndrome. In addition, Propantheline inhibits gastrointestinal propulsive motility and decreases gastric acid secretion and controls excessive pharyngeal, tracheal and bronchial secretions.
Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)|Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)
Approximately 70% of the dose is excreted in the urine, mostly as metabolites.|AFTER 95 HR HUMANS EXCRETED IN URINE 5% OF DOSE (0.03 G) OF PROPANTHELINE BROMIDE GIVEN ORALLY. /PROPANTHELINE BROMIDE, FROM TABLE/|The quarternary ammonium derivatives of the belladonna alkaloids are poorly absorbed after an oral dose; nevertheless, some of these compounds applied locally to the eye can cause mydriasis and cycloplegia. /Quarternary ammonium derivatives of belladonna alkaloids/
Action is achieved via a dual mechanism: (1) a specific anticholinergic effect (antimuscarinic) at the acetylcholine-receptor sites and (2) a direct effect upon smooth muscle (musculotropic).|ANTICHOLINERGIC DRUGS BLOCK THE ACTION OF ACETYLCHOLINE AT POSTGANGLIONIC CHOLINERGIC SITES, THEREBY INCREASING BLADDER CAPACITY BY REDUCING THE NUMBER OF MOTOR IMPULSES REACHING THE DETRUSOR MUSCLE. /ANTICHOLINERGIC DRUGS/
Only tests relating to glaucoma apparently have consisted of admin doses of 15 mg ... orally to 20 normal patients and to 20 patients with various kinds of glaucoma and evaluating intraocular pressure by tonometry performed hourly for 3 hr. ... Tension did not change in normal eyes ... . /Propantheline bromide/|Symptoms and signs of drug abuse: Vital signs - temperature elevated; heart rate increased; possibly decreased blood pressure. Mental status - drowsiness or coma, sensorium clouded, amnesia, disorientation, visual hallucinations, body image alterations, confusion; with propantheline, restlessness, excitement. /Anticholinergic agents, from table/|VERY HIGH DOSES BLOCK THE SKELETAL NEUROMUSCULAR JUNCTION. THE USUAL CLINICAL DOSE ... ACTS FOR ABOUT 6 HOURS.|An elderly woman presented with preumonia and mental status changes and was found to have bromide /intoxication/ due to ingestion of propantheline bromide over a 2 mo period. The interference of bromide with serum chloride measurements on ion selective electrode resulted in spurious hyperchloremia and was crucial in making the diagnosis. /Propantheline bromide/
Bromide, Propantheline
Propantheline Use and Manufacturing
Cusic, Robinson, J Org Chem (16) 1921, 1951; US patent 2,659,732 (1953 to Searle). /Bromide/|Prepared by reacting xanthene-9-carboxylic acid chloride with 2-diisopropylaminoethanol, followed by alkylation with methyl bromide. /Bromide/
Anticholinergic.
Corrigast; Ercotina; Pro-Banthine; Neo-Metantyl; Pantheline|BETA-DIISOPROPYLAMINOETHYL 9-XANTHENECARBOXYLATE METHOBROMIDE; (2-HYDROXYETHYL)DIISOPROPYLMETHYLAMMONIUM BROMIDE XANTHENE-9-CARBOXYLATE; NEOPEPULSAN; PRO-BANTHINE BROMIDE; PROPANTHELINE BROMIDE; XANTHENE-9-CARBOXYLIC ACID, ESTER WITH (2-HYDROXYETHYL)DIISOPROPYLMETHYLAMMONIUM BROMIDE. /BROMIDE/
Listed in the U.S. Pharmacopeia. /Bromide/
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Computed Properties
Molecular Weight:368.5
XLogP3:4.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:7
Exact Mass:368.22256882
Monoisotopic Mass:368.22256882
Topological Polar Surface Area:35.5
Heavy Atom Count:27
Formal Charge:1
Complexity:474
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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