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HCID 31101생성일: 2026년 10월 27일

Bromocriptine

Parlodel · bromocryptine · bromoergocryptine · BROMOCRITINE · 2-bromo-ergocryptin · Kripton · SAN 15-754 · bromocriptin

https://huagongshe.com/ko/chemical/31101

Bromocriptine 분자 구조식

식별자 및 물리적 특성

CAS No.25614-03-3
분자식C32H40BrN5O5
평균 분자량654.6 g/mol
단동위원소 질량653.22128 g/mol
SMILESCC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C=C4c5cccc6[nH]c(Br)c(c56)C[C@H]4N(C)C3)(C(C)C)C(=O)N12
InChIKeyOZVBMTJYIDMWIL-AYFBDAFISA-N
PubChem CID31101
ChEMBLCHEMBL311816
ChEBICHEBI:3181
EC No.247-128-5
DTXSIDDTXSID1022687

화학 및 물리적 성질

XLogP3.8
극성 표면적118
수소 결합 공여자 수3
수소 결합 수용자 수6
회전 가능 결합 수5
무거운 원자 수43
형식 전하0
복잡도1,230
의약품Pharmaceuticals -> Listed in ZINC15
LogP(분배 계수)3.54.61
용해도8.58e-02 g/L
Human DrugsBreast FeedingLactationMilk, HumanAntiparkinson AgentsDopamine AgonistsErgot AlkaloidsPharmaceuticalsMedicines for central nervous system disorders
Endocrine DisruptorsPotential endocrine disrupting compound
녹는점215-218215-218° (dec)
Physical DescriptionSolid
Collision Cross Section248.5 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID6020197]243.09 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
끓는 점891.3±65.0 °C(Predicted)
밀도1.2734 (rough estimate)
굴절률1.6400 (estimate)
pKa(산도 계수)pKa 4.90±0.05(80% MCS t = RT) (Uncertain)
용해도2.07mg/L(온도 미공개)
InChIKeyOZVBMTJYIDMWIL-CCCBMRMVNA-N
SMILESN12[C@@H](CC(C)C)C(N3CCC[C@@]3([H])[C@]1(O)O[C@@](C(C)C)(NC(=O)[C@H]1CN([C@]3([H])CC4=C(NC5C=CC=C(C4=5)C3=C1)Br)C)C2=O)=O |&1:1,11,13,16,23,26,r|

화학적 성질

Crystals.

안전 및 규제

GHS 분류WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P263, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
기타 안전 정보IMAP assessments - Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'.alpha.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
TreatmentTreatment of overdose consists of removal of the drug by emesis (if conscious), gastric lavage, activated charcoal, or saline catharsis. Careful supervision and recording of fluid intake and output is essential. Hypotension should be treated by placing the patient in the Trendelenburg position and administering I.V. fluids. If satisfactory relief of hypotension cannot be achieved by using the above measures to their fullest extent, vasopressors should be considered. (L1827)
건강 영향A slight hypotensive effect may accompany bromocriptine treatment. Few cases of cerebrospinal fluid rhinorrhea have been reported in patients receiving bromocriptine for treatment of large prolactinomas. Bromocriptine use has been associated with causing or worsening psychotic symptoms and fibrosis of multiple organs. Ingestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A2913, L1827, L1934)
HepatotoxicityBromocriptine has been reported to cause serum aminotransferase elevations in a small proportion of patients, but these abnormalities are usually mild, asymptomatic and self-limiting even without dose adjustment. In rare instances, more marked elevations occur that may require dose modification or discontinuation and which can recur with rechallenge. In addition, bromocriptine has been implicated in a small number of cases of clinically apparent acute liver injury, but the clinical characteristics and typical pattern of enzyme elevations has not been characterized and case reports of hepatic injury due to bromocriptine have not been published. Thus, bromocriptine is a very rare cause of clinically apparent liver injury and has not been implicated in causing acute liver failure or chronic liver injury.
유해 작용Common Adverse Effects

용도

용도

Bromocriptine, a dopaminomimetic that is a dopamine D2 receptor agonist, possesses expressed antiparkinsonian activity. It is used for treating all phases of idiopathic and postencephalic Parkinsonism.

노출 경로Oral (L1934). Approximately 28% of the oral dose is absorbedhowever due to a substantial first pass effect, only 6% of the oral dose reaches the systemic circulation unchanged. Bromocriptine and its metabolites appear in the blood as early as 10 minutes following oral administration and peak plasma concentration are reached within 1-1.5 hours. Serum prolactin may be decreased within 2 hours or oral administration with a maximal effect achieved after 8 hours. Growth hormone concentrations in patients with acromegaly is reduced within 1-2 hours with a single oral dose of 2.5 mg and decreased growth hormone concentrations persist for at least 4-5 hours.
독성 요약Signs and Symptoms of OverdoseThe dopamine D<sub>2</sub> receptor is a 7-transmembrane G-protein coupled receptor associated with G<sub>i</sub> proteins. In lactotrophs, stimulation of dopamine D<sub>2</sub> receptor causes inhibition of adenylyl cyclase, which decreases intracellular cAMP concentrations and blocks IP3-dependent release of Ca<sup>2+</sup> from intracellular stores. Decreases in intracellular calcium levels may also be brought about via inhibition of calcium influx through voltage-gated calcium channels, rather than via inhibition of adenylyl cyclase. Additionally, receptor activation blocks phosphorylation of p42/p44 MAPK and decreases MAPK/ERK kinase phosphorylation. Inhibition of MAPK appears to be mediated by c-Raf and B-Raf-dependent inhibition of MAPK/ERK kinase. Dopamine-stimulated growth hormone release from the pituitary gland is mediated by a decrease in intracellular calcium influx through voltage-gated calcium channels rather than via adenylyl cyclase inhibition. Stimulation of dopamine D<sub>2</sub> receptors in the nigrostriatal pathway leads to improvements in coordinated muscle activity in those with movement disorders. Ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Bromocriptine acts by directly stimulating the dopamine receptors in the corpus striatum. (A2914, A2915, A2916, A2941)
Signs and SymptomsSide effects of bromocriptine include nausea, headache, dizziness, fatigue, lightheadedness, vomiting, abdominal cramps, nasal congestion, constipation, diarrhea and drowsiness. Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (L1920, L1827)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)bromocriptineDILI PositiveOralDOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for PharmaceuticalsBromocriptine0.10.2The initial dosage of bromocriptine mesylate tablets in adults is one-half to one 2.5 mg scored tablet daily. An additional 2.5 mg tablet may be added to the treatment regimen as tolerated every 2-7 days until an optimal therapeutic response is achieved. The therapeutic dosage ranged from 2.5-15 mg daily in adults studied clinically.Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 2.5 mg/day, Lowest Therapeutic Dose (LTD): 0.03 mg/kg-day, and Screening Dose: 0.00001 mg/kg-day.4-May-07
독성An ergot alkaloid derivative that exhibits potent dopamine agonist properties, particularly at D2 dopamine receptors. Bromocriptine, like dopamine, inhibits prolactin release from the pituitary and so is used in endocrine disorders, such as hyperprolactinemia. It is also used in the treatment of Parkinson’s disease. A large “first-pass” effect is seen with bromocriptine, and peak concentrations occur about 1.5-3 h after ingestion, with a half-life of about 3 h. Nausea, vomiting, and orthostatic hypotension are among the acute adverse effects. Long-term use has been associated with dyskinesias, constipation, psychoses, digital spasm, and erythromelalgia. The LD50 in rabbits exceeds 1 g/kg, p.o., and 12 mg/kg, i.v.