Basic information
- CAS
54-71-7- Standard SMILES
CC[C@@H]1C(=O)OC[C@@H]1Cc1cncn1C.Cl- InChIKey
RNAICSBVACLLGM-GNAZCLTHSA-N- Molecular formula
- C11H17ClN2O2
- Average molar mass
- 244.72 g/mol
- Monoisotopic mass
- 244.09785546
Overview
Pilocarpine hydrochloride is the hydrochloride salt of (+)-pilocarpine, a medication used to treat increased pressure inside the eye and dry mouth. It contains a (+)-pilocarpine.
Names & identifiers
- Preferred name
- Pilocarpine Hydrochloride
- IUPAC
- (3S,4R)-3-ethyl-4-[(3-methylimidazol-4-yl)methyl]oxolan-2-one;hydrochloride
- English name
- (+)-Pilocarpine hydrochloride
- Molecular formula
- C11H17ClN2O2
- Molecular weight
- 244.72
Names & synonyms
Pilocarpine hydrochloride54-71-7Pilocarpine HClSalagenPilocarpine monohydrochlorideSno piloIsopto carpineVistacarpin NPILOPINE HSPilopineQLOSIVUITY
Show more names
(3S,4R)-4,5-DIHYDRO-3-ETHYL-4-(1-METHYL-1H-IMIDAZOL-5-YLMETHYL)-2(3H)-FURANONE HYDROCHLORIDESanpilopilocarpilocel(3S,4R)-Akarpineami-pilo
Pilocarpinum muriaticum0WW6D218XJNSC5746CHEBI:141029Pilocarpini hydrochloridumDTXSID2041096(3S,4R)-3-ethyl-4-((1-methyl-1H-imidazol-5-yl)methyl)dihydrofuran-2(3H)-one hydrochloride2(3H)-Furanone, 3-ethyldihydro-4-((1-methyl-1H-imidazol-5-yl)methyl)-, monohydrochloride, (3S,4R)-
Database identifiers
- CAS
54-71-7- PubChem CID
- 5909
- DTXSID
DTXSID2041096- ChEMBL
CHEMBL1200330、CHEMBL611494- ChEBI
CHEBI:141029- UNII
- 0WW6D218XJ
- EC Number
- 200-212-5
Properties
Computed structural properties
- Topological polar surface area
- 44.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 245
Experimental & physicochemical properties
Solubility>36.7 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 202 · 202-205 °C(lit.)
- alpha
- 89 · 89 º (C=5, H2O)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: 100 mg/mL
- form
- powder
- color
- white
- optical activity
- 91.7 · +91.7 (H2O)
- Water Solubility
- soluble
- Sensitive
- Hygroscopic
- Merck
- 14 · 14,7424
- BRN
- 4034491 · 4034491
- Stability
- Hygroscopic
- Major Application
- forensics and toxicologyveterinary
- InChI
- 1S/C11H16N2O2.ClH/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2;/h5,7-8,10H,3-4,6H2,1-2H3;1H/t8-,10-;/m0./s1
- InChIKey
- RNAICSBVACLLGM-GNAZCLTHSA-N
- SMILES
- Cl.CC[C@H]1[C@H](COC1=O)Cc2cncn2C
- LogP
- -0.095 · -0.095 (est)
- CAS DataBase Reference
- 54 · 54-71-7(CAS DataBase Reference)
- FDA UNII
- 0 WW6D218XJ · 0WW6D218XJ
- NCI Drug Dictionary
- pilocarpine hydrochloride
- EPA Substance Registry System
- Pilocarpine monohydrochloride (54-71-7)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300+H330
- Precautionary statements
- 301 · P301+P310+P330-P304+P340+P310
- Hazard Codes
- T+,T
- Risk Statements
- 26 · 26/28-25-23
- Safety Statements
- 25 · 25-45
- RIDADR
- 1544 · UN 1544 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 1450000 · TK1450000
- F
- 3 · 3-8-10
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29399990 · 29399990
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 2 InhalationAcute · Acute Tox. 2 InhalationAcute Tox. 2 Oral
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (64.2%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P264, P270, P271, P284, P301+P316, P304+P340, P316, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 123 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationPilocarpine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, monohydrochloride, (3S-cis)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 2 (64.2%)
Toxicology
Treatment
Overdosage should be treated with atropine titration (0. 5 mg to 1. 0 mg given subcutaneously or intravenously) and supportive measures to maintain respiration and circulation. Epinephrine (0. 3 mg to 1. 0 mg, subcutaneously or intramuscularly) may also be of value in the presence of severe cardiovascular depression or bronchoconstriction. (L1712)
Exposure RoutesOral ; eye contact. There was a decrease in the rate of absorption of pilocarpine from SALAGEN Tablets when taken with a high fat meal by 12 healthy male volunteers
Toxicity Summary
Pilocarpine is a cholinergic parasympathomimetic agent. It increase secretion by the exocrine glands, and produces contraction of the iris sphincter muscle and ciliary muscle (when given topically to the eyes) by mainly stimulating muscarinic receptors.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- F
- 3-8-10
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- TK1450000
- ridadr
- UN 1544 6.1/PG 3
- hs_code
- 29399990
- risk_code
- 26/28-25-23
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+,T
- safety_code
- 25-45
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- III
- Hazard statements
- H300+H330
- Hazard Classifications
- Acute Tox. 2 InhalationAcute Tox. 2 Oral
- Precautionary statements
- P301+P310+P330-P304+P340+P310
Chemistry & industry
Pharmacology
Metabolism/MetabolitesPossibly occurs at the neuronal synapses and in the plasma
Half Life: 0.76 hours
FDA Pharmacological Classification
PILOCARPINE HYDRCHLORIDE
Cholinergic Agonists [MoA]; Cholinergic Receptor Agonist [EPC]; Cholinergic Muscarinic Agonists [MoA]
PILOCARPINE HYDROCHLORIDE
Cholinergic Agonists [MoA]; Cholinergic Receptor Agonist [EPC]; Cholinergic Muscarinic Agonists [MoA]
PILOCARPINE HYDROCHLORIDE OPHTHALMIC SOLUTION
Cholinergic Muscarinic Agonists [MoA]; Cholinergic Receptor Agonist [EPC]; Cholinergic Agonists [MoA]
MeSH Pharmacological Classification
Agents causing contraction of the pupil of the eye. Some sources use the term miotics only for the parasympathomimetics but any drug used to induce miosis is included here.
Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate.
Uses & manufacturing
UsesFor the treatment of radiation-induced dry mouth (xerostomia) and symptoms of dry mouth in patients with Sjögrens syndrome.
General Manufacturing Information2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, hydrochloride (1:1), (3S,4R)-: ACTIVE
Applications
DescriptionIt is a bioactive chemical usually used as pharmaceutical agents such as acetylcholine receptor agonist, antiglaucoma agent, moitic, and sialogogue. Specifically, due to its desirable activity as acetylcholine receptor agonist, this chemical has been introduced to regulate muscarinic acetylcholine receptor function in acetylcholinesterase knockout mice.1 Moreover, because of its good antiglaucoma effect, this substance is applied in a timolol plus maximum-tolerated antiglaucoma therapy.2 In addition, this chemical has been demonstrated to show a favourable miotic activity when incorporated into polymer capsules.3 Besides, this compound can be utilized to relieve the xerostomia due to chronic graft-versus-host disease or total-body irradiation after bone-marrow transplantation for hematologic malignancies.4
UsesAntiglaucoma agent; miotic; sialogogue.
Uses(+)-Pilocarpine hydrochloride is a muscarinic M1 and M2 acetylcholine receptor agonist with pKB values of 5 and 3.7, respectively. Systemic administration of (+)-Pilocarpine hydrochloride is typically used as an animal model for temporal lobe epilepsy and can mimic the generation of complex partial seizures by producing changes in hippocampal neuron morphology, membrane properties, and synaptic responses.
General DescriptionPilocarpine monohydrochlorideis the hydrochloride of an alkaloid obtainedfrom the dried leaflets of Pilocarpus jaborandi or P. microphyllus,in which it occurs to the extent of about 0.5% togetherwith other alkaloids.
Upstream & downstream products
Upstream raw materials
Suppliers104 total
北京华美互利生物化工010-56205725 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
成都健腾生物技术有限公司028-85159085 18080455027 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
江苏星科元信息科技有限公司400-605-7200 15335295587 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
南京望知星医药科技有限公司18569809817 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎（中国）化学有限公司400-6106006 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
InvivoChem中国13549236410 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
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广东谦进化学试剂有限公司0751-2818792 13435114148 · [email protected]
ChemeGen 中国18818260767 · [email protected]
HONG KONG IPURE BIOLOGY CO.,LIMITED86 18062405514 18062405514 · [email protected]
上海耐士化工科技有限公司400-188-0725 +86 21 34310725 13611771617
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TCI AMERICA800-4238616 · [email protected]
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TCI Europe320-37350700 · [email protected]
苏州亚科科技股份有限公司0512-87182055 13451648594 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
成都润泽本土化工有限公司13096311329 028-88469284 616445927 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
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Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
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上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Additional notes
DefinitionChEBI: Pilocarpine hydrochloride is the hydrochloride salt of (+)-pilocarpine, a medication used to treat increased pressure inside the eye and dry mouth. It contains a (+)-pilocarpine.
Related reactions
3 records
Compound notes
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