Pimecrolimus

Các tên gọi khác (3) :

33-Epi-chloro-33-desoxyascomycin
Pimecrolimus
Pimecrolimusum

anti inflammatory agents non steroidal, dermatologic agents, immunosuppressive agents

Thuốc Gốc

Small Molecule

CAS: 137071-32-0

ATC: D11AH02

ĐG : Novartis AG , http://www.novartis.com

CTHH: C₄₃H₆₈ClNO₁₁

PTK: 810.453

Pimecrolimus is an immunomodulating agent used in the treatment of atopic dermatitis (eczema). It is currently available as a topical cream, once marketed by Novartis, (however Galderma will be promoting the molecule in Canada in early 2007) under the trade name Elidel. [Wikipedia]

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₄₃H₆₈ClNO₁₁

Phân tử khối

810.453

Monoisotopic mass

809.44808973

InChI

InChI=1S/C43H68ClNO11/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)45-16-12-11-13-32(45)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-31(44)35(22-29)52-7/h18,20,25,27-33,35-39,46,51H,10-17,19,21-23H2,1-9H3/b24-18-,26-20+/t25-,27+,28-,29-,30+,31-,32-,33-,35+,36-,37-,38+,39+,43+/m0/s1

InChI Key

InChIKey=KASDHRXLYQOAKZ-KDCWXYOMSA-N

IUPAC Name

(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-12-[(1E)-1-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0^{4,9}]octacos-18-ene-2,3,10,16-tetrone

Traditional IUPAC Name

SMILES

[H][C@]12O[C@](O)([C@H](C)C[C@@H]1OC)C(=O)C(=O)N1CCCC[C@@]1([H])C(=O)O[C@@H]([C@@H](C)[C@@H](O)CC(=O)[C@H](CC)\C=C(C)/C[C@H](C)C[C@@H]2OC)C(\C)=C\[C@@H]1CC[C@H](Cl)[C@@H](C1)OC

Độ hòa tan

1.52e-03 g/l

logP

4.4

logS

-5.7

pKa (strongest acidic)

9.96

pKa (Strongest Basic)

-2.9

PSA

158.13 Å²

Refractivity

214.03 m³·mol^-1

Polarizability

87.87 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

MDDR-Like Rule

true

Dược Lực Học : Pimecrolimus is a chemical that is used to treat atopic dermatitis (eczema). Atopic dermatitis is a skin condition characterized by redness, itching, scaling and inflammation of the skin. The cause of atopic dermatitis is not known; however, scientists believe that it may be due to activation of the immune system by various environmental or emotional triggers. Scientists do not know exactly how pimecrolimus reduces the manifestations of atopic dermatitis, but pimecrolimus reduces the action of T-cells and mast cells which are part of the immune system and contribute to responses of the immune system. Pimecrolimus prevents the activation of T-cells by blocking the effects of chemicals (cytokines) released by the body that stimulate T-cells. Pimecrolimus also reduces the ability of mast cells to release chemicals that promote inflammation.

Cơ Chế Tác Dụng : Pimecrolimus is an immunomodulating agent used in the treatment of atopic dermatitis (eczema). It is currently available as a topical cream, once marketed by Novartis, (however Galderma will be promoting the molecule in Canada in early 2007) under the trade name Elidel. [Wikipedia] Pimecrolimus binds with high affinity to macrophilin-12 (FKBP-12) and inhibits the calcium-dependent phosphatase, calcineurin. As a consequence, it inhibits T cell activation by blocking the transcription of early cytokines. In particular, pimecrolimus inhibits at nanomolar concentrations Interleukin-2 and interferon gamma (Th1-type) and Interleukin-4 and Interleukin-10 (Th2-type) cytokine synthesis in human T cells. Also, pimecrolimus prevents the release of inflammatory cytokines and mediators from mast cells in vitro after stimulation by antigen/lgE.

Dược Động Học :

▧ Absorption :
Because of the low systemic absorption of pimecrolimus following topical application the calculation of standard pharmacokinetic measures such as AUC, C_max, half-life, etc. cannot be reliably done.
▧ Protein binding :
74%-87% (in vitro, bound to plasma proteins)
▧ Metabolism :
No drug metabolism was observed in human skin in vitro. Oral administration yielded metabolites produced from O-demethylation and oxygenation reactions.
▧ Route of Elimination :
80% of the drug is excreted in the feces.

Độc Tính : Side effects include burning sensation, irritation, pruritus, erythema, and skin infections, at the application site.

Chỉ Định : For treatment of mild to moderate atopic dermatitis.

Tương Tác Thuốc :

Abatacept Avoid combination due to enhanced adverse effects of immunosuppressive agents.
ado-trastuzumab emtansine Avoid combination due to the increase in immunosuppressant side effects.
Antithymocyte globulin Avoid combination due to enhanced immunosuppressive effects and increased risk of infections.
Belatacept Avoid combination due to enhanced effects of immunosuppressants.
Belimumab Avoid combination due to enhanced toxic effects of immunosuppressants.
Bleomycin Pimecrolimus may enhance the adverse/toxic effect of immunosuppressants like bleomycin. This combination is contraindicated
Brentuximab vedotin Avoid combination due to the potential enhancement of toxic effects of immunosuppressants
Canakinumab Avoid combination due the potential increase in immunosuppressant adverse effects.
Carboplatin Pimecrolimus may enhance the adverse/toxic effect of immunosuppressants such as carboplatin. Avoid use of pimecrolimus cream in patients receiving immunosuppressants.
Carmustine Pimecrolimus may enhance the adverse/toxic effect of immunosuppressants such as carmustine. Avoid use of pimecrolimus cream in patients receiving immunosuppressants.
Chlorambucil Pimecrolimus may enhance the adverse/toxic effect of immunosuppressants such as chlorambucil. Avoid use of pimecrolimus cream in patients receiving immunosuppressants.
Cisplatin Pimecrolimus may enhance the adverse/toxic effect of immunosuppressants such as cisplatin. Avoid use of pimecrolimus cream in patients receiving immunosuppressants.
Cladribine Pimecrolimus may enhance the adverse/toxic effect of immunosuppressants such as cladribine. Avoid use of pimecrolimus cream in patients receiving immunosuppressants.
Clofarabine Pimecrolimus may enhance the adverse/toxic effect of immunosuppressants such as clofarabine. Avoid use of pimecrolimus cream in patients receiving immunosuppressants.
Etanercept Avoid combination due to enhanced immunosuppressive effects.
Gemtuzumab ozogamicin Avoid combination due to toxic effects of immunosuppressants.
Glatiramer Acetate Avoid combination due to enhanced immunosuppressive effects.
golimumab Avoid combination due to enhancement of side effects from immunosuppressants.
Homoharringtonine Avoid combination as there is potential to increase immunosuppressant adverse effects.
Ibritumomab Avoid combination due to increased immunosuppressive effects.
Infliximab Pimecrolimus enhances the adverse effects of immune suppressants thus the combination should be avoided.
Obinutuzumab Avoid combination due to enhanced immunosuppressive effects.
Omalizumab Avoid combination due to enhanced adverse effects of immunosuppressants.
Paclitaxel Avoid combination due to the enhancement of adverse effects of immunosuppressants.
Pegaspargase Avoid combination because pimecrolimus enhances the adverse effects of immunosuppressants.
Teriflunomide Avoid combination due to the increased toxic effects of immunosuppressants.
Tofacitinib Avoid combination due to the potential increase in immunosuppressant associated adverse effects.

Liều Lượng & Cách Dùng : Cream - Topical

Dữ Kiện Thương Mại

Giá thị trường

Biệt dược thương mại : Elidel 1% cream

Giá bán buôn : USD >3.21

Đơn vị tính : g
Biệt dược thương mại : Elidel 30 Gram Tube 1% 30 gm Tube

Giá bán buôn : USD >101.44

Đơn vị tính : tube
Biệt dược thương mại : Elidel 60 Gram Tube 1% 60 gm Tube

Giá bán buôn : USD >200.05

Đơn vị tính : tube
Biệt dược thương mại : Elidel 100 Gram Tube 1% 100 gm Tube

Giá bán buôn : USD >315.76

Đơn vị tính : tube

Nhà Sản Xuất

Công ty : Meda Pharm

Sản phẩm biệt dược : Aregen
Công ty : Valeant

Sản phẩm biệt dược : Elidel
Công ty : Esteve

Sản phẩm biệt dược : Rizan

Đóng gói

Công ty : Novartis AG

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

Website : http://www.physicianstotalcare.com

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB00337

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=17753757

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505748

National Drug Code Directory

http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0078-0375-46

PharmGKB

http://www.pharmgkb.org/drug/PA164783790

Wikipedia

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

RxList

http://www.rxlist.com/cgi/generic/elidel.htm

PDRhealth

http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/eli1609.shtml

Drugs.com

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

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