Reserpine

Các tên gọi khác (8 ) :

(-)-Reserpine
(−)-reserpine
(3beta,16beta,17alpha,18beta,20alpha)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
3,4,5-trimethoxybenzoyl methyl reserpate
Apoplon
Reserpin
Reserpine
Serpalan

antihypertensive agents, adrenergic uptake inhibitors, antipsychotic agents, adrenergic antagonists

Thuốc Gốc

Small Molecule

CAS: 50-55-5

ATC: C02AA02

ĐG : Apotheca Inc.

CTHH: C₃₃H₄₀N₂O₉

PTK: 608.6787

An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use. [PubChem]

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₃₃H₄₀N₂O₉

Phân tử khối

608.6787

Monoisotopic mass

608.273380888

InChI

InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1

InChI Key

InChIKey=QEVHRUUCFGRFIF-MDEJGZGSSA-N

IUPAC Name

methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(3,4,5-trimethoxyphenyl)carbonyloxy]-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Traditional IUPAC Name

reserpine

SMILES

[H][C@]12C[C@@H](OC(=O)C3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=C3C=CC(OC)=C1)C2

Độ tan chảy

264.5 °C

Độ hòa tan

73 mg/L (at 30 °C)

logP

3.2

logS

-4.7

pKa (strongest acidic)

16.29

pKa (Strongest Basic)

7.56

PSA

117.78 Å²

Refractivity

161.42 m³·mol^-1

Polarizability

66.05 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

MDDR-Like Rule

true

pKa

6.6

Dược Lực Học : Reserpine is an adrenergic blocking agent used to treat mild to moderate hypertension via the disruption of norepinephrine vesicular storage. The antihypertensive actions of Reserpine are a result of its ability to deplete catecholamines from peripheral sympathetic nerve endings. These substances are normally involved in controlling heart rate, force of cardiac contraction and peripheral resistance.

Cơ Chế Tác Dụng : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use. [PubChem] Reserpine's mechanism of action is through inhibition of the ATP/Mg²⁺ pump responsible for the sequestering of neurotransmitters into storage vesicles located in the presynaptic neuron. The neurotransmitters that are not sequestered in the storage vesicle are readily metabolized by monoamine oxidase (MAO) causing a reduction in catecholamines.

Dược Động Học :

▧ Protein binding :
62%
▧ Route of Elimination :
Reserpine is extensively metabolized to inactive compounds. It is slowly excreted via the urine and feces.

Độc Tính : Possible human carcinogen. May cause reproductive harm. ORL-RAT LD₅₀ 420 mg/kg; IPR-RAT LD₅₀ 44 mg/kg; IVN-RAT LD₅₀ 15 mg/kg; ORL-MUS LD₅₀ 200 mg/kg; SCU-MUS LD₅₀ 52 mg/kg; IPR-RBT LD₅₀ 7 mg/kg

Chỉ Định : Foe the treatment of hypertension

Tương Tác Thuốc :

Dobutamine Increased arterial pressure
Dopamine Increased arterial pressure
Ephedra Increased arterial pressure
Ephedrine Increased arterial pressure
Epinephrine Increased arterial pressure
Fenoterol Increased arterial pressure
Iobenguane May diminish the therapeutic effect and increase chances of producing a false negative imaging result of Iobenguane as it depletes or inhibit reuptake of noradrenaline stores
Isoprenaline Increased arterial pressure
Mephentermine Increased arterial pressure
Metaraminol Increased arterial pressure
Methoxamine Increased arterial pressure
Norepinephrine Increased arterial pressure
Orciprenaline Increased arterial pressure
Phenylephrine Increased arterial pressure
Phenylpropanolamine Increased arterial pressure
Pirbuterol Increased arterial pressure
Procaterol Increased arterial pressure
Pseudoephedrine Increased arterial pressure
Salbutamol Increased arterial pressure
Terbutaline Increased arterial pressure
Tetrabenazine Reserpine may increase the adverse/toxic effects of tetrabenazine as they have similar pharmacologic properties. Concomitant therapy is contraindicated.
Topotecan The p-glycoprotein inhibitor, Reserpine, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
Tranylcypromine Addition of Reserpine to Tranylcypromine therapy may induce paradoxical Reserpine effects, including peripheral hypertension and central exciation. Close monitoring for adverse effects is required. Addition of Tranylcypromine to Reserpine therapy may be less of a concern.
Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Triprolidine The CNS depressants, Triprolidine and Reserpine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.

Liều Lượng & Cách Dùng : Tablet - Oral

Dữ Kiện Thương Mại

Giá thị trường

Biệt dược thương mại : Reserpine 0.25 mg tablet

Giá bán buôn : USD >1.52

Đơn vị tính : tablet
Biệt dược thương mại : Reserpine 0.1 mg tablet

Giá bán buôn : USD >0.83

Đơn vị tính : tablet

Nhà Sản Xuất

Công ty :

Sản phẩm biệt dược : Apoplon
Công ty :

Sản phẩm biệt dược : Hiserpia
Công ty :

Sản phẩm biệt dược : Novoreserpine
Công ty :

Sản phẩm biệt dược : Reserfia
Công ty :

Sản phẩm biệt dược : Serpalan
Công ty :

Sản phẩm biệt dược : Serpanray
Công ty :

Sản phẩm biệt dược : Serpasil

Đóng gói

Công ty : Apotheca Inc.
Công ty : C.O. Truxton Inc.
Công ty : Carlisle Laboratories Inc.
Công ty : Dispensing Solutions

Website : http://www.drxdispensing.com
Công ty : Eon Labs
Công ty : H and H Laboratories

Website : http://www.hhlabs.com
Công ty : Major Pharmaceuticals

Website : http://www.majorpharmaceuticals.com
Công ty : Murfreesboro Pharmaceutical Nursing Supply

Website : http://www.unitdosesupply.com
Công ty : Physicians Total Care Inc.

Website : http://www.physicianstotalcare.com
Công ty : Quality Research Pharmaceutical Inc.
Công ty : United Research Laboratories Inc.

Website : http://www.urlpharma.com

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB00206

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5770

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505863

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C06539

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D00197

ChemSpider

http://www.chemspider.com/Chemical-Structure.5566.html

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0185-0032-01

PharmGKB

http://www.pharmgkb.org/drug/PA451236

Wikipedia

http://en.wikipedia.org/wiki/Reserpine

Drugs.com

http://www.drugs.com/cdi/reserpine.html

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