CORTIVAZOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H38N2O5
Molecular Weight	530.6545
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@H](C)[C@](O)(C(=O)COC(C)=O)[C@@]1(C)C[C@H](O)[C@@]3([H])[C@@]2([H])C=C(C)C4=CC5=C(C[C@]34C)C=NN5C6=CC=CC=C6

InChI

InChIKey=RKHQGWMMUURILY-UHRZLXHJSA-N

InChI=1S/C32H38N2O5/c1-18-11-23-25-12-19(2)32(38,28(37)17-39-20(3)35)31(25,5)15-27(36)29(23)30(4)14-21-16-33-34(26(21)13-24(18)30)22-9-7-6-8-10-22/h6-11,13,16,19,23,25,27,29,36,38H,12,14-15,17H2,1-5H3/t19-,23+,25+,27+,29-,30+,31+,32+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2205477 | https://www.ncbi.nlm.nih.gov/pubmed/16158972 | https://www.has-sante.fr/portail/upload/docs/application/pdf/2015-10/altim_version_anglaise_ct13633_def.pdf | https://www.ncbi.nlm.nih.gov/pubmed/1239292

The phenylpyrazosteroid cortivazol is a selective agonist ligand for the glucocorticoid receptor (GR), a steroid receptor member of the nuclear receptor superfamily of transcription factors. Cortivazol is an apoptotic, anti-inflammatory and immunosuppressive agent that has been used in the treatment of diskogenic radiculopathy, back pain, osteoarthritis and acute childhood lymphoblastic leukemia. Cortivazol has potent antileukemic activity in childhood ALL. Its activity is related to cell cycle arrest and induction of apoptosis. Cortivazol (Altim) is indicated in rheumatological diseases: - In intra-articular injection: inflammatory arthritis, advanced osteoarthritis. - In periarticular injection: tendinitis, bursitis. - In injection of soft tissue: talalgia, carpal tunnel syndrome, Dupuytren’s contracture. - In epidural injection: radiculalgia

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17606285 \| https://www.ncbi.nlm.nih.gov/pubmed/4029081 \| https://www.ncbi.nlm.nih.gov/pubmed/2702665 \| https://www.ncbi.nlm.nih.gov/pubmed/2880860	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://www.has-sante.fr/portail/upload/docs/application/pdf/2015-10/altim_version_anglaise_ct13633_def.pdf	Primary		Approved 8429	ALTIM Approved Use This product is indicated in rheumatological diseases: - In intra-articular injection: inflammatory arthritis, advanced osteoarthritis. - In periarticular injection: tendinitis, bursitis. - In injection of soft tissue: talalgia, carpal tunnel syndrome, Dupuytren’s contracture. - In epidural injection: radiculalgia
Musculoskeletal and joint disorders 3 Sources: http://en.pharmacodia.com/web/drug/1_11814.html https://www.drugs.com/international/altim.html https://www.vidal.fr/actualites/20916/altim_cortivazol_arret_de_production_et_d_approvisionnement_pour_une_duree_indeterminee/	Primary		Approved 8429	ALTIM Approved Use This product is indicated in rheumatological diseases: - In intra-articular injection: inflammatory arthritis, advanced osteoarthritis. - In periarticular injection: tendinitis, bursitis. - In injection of soft tissue: talalgia, carpal tunnel syndrome, Dupuytren’s contracture. - In epidural injection: radiculalgia

PubMed

Title	Date	PubMed
[Superficial injections of anti-inflammatory drugs and severe infectious complications].	2001 May 5-12	11402940
Distinct interaction of cortivazol with the ligand binding domain confers glucocorticoid receptor specificity: cortivazol is a specific ligand for the glucocorticoid receptor.	2002 Feb 15	11741935
Synthesis of halogen-substituted pyridyl and pyrimidyl derivatives of [3,2-c]pyrazolo corticosteroids: strategies for the development of glucocorticoid receptor mediated imaging agents.	2002 Nov 21	12431067
Better results with rhenium-186 radiosynoviorthesis than with cortivazol in rheumatoid arthritis (RA): a two-year follow-up randomized controlled multicentre study.	2004 Sep-Oct	15485015
The distinct agonistic properties of the phenylpyrazolosteroid cortivazol reveal interdomain communication within the glucocorticoid receptor.	2005 May	15677712
Cytotoxicity of cortivazol in childhood acute lymphoblastic leukemia.	2005 May-Jun	16158972
Gene expression profiling of leukemic cells and primary thymocytes predicts a signature for apoptotic sensitivity to glucocorticoids.	2007 Nov 28	18045478
Systemic effects of epidural and intra-articular glucocorticoid injections in diabetic and non-diabetic patients.	2007 Oct	17919959
Comparison of two structurally diverse glucocorticoid receptor agonists: cortivazol selectively regulates a distinct set of genes separate from dexamethasone in CEM cells.	2007 Sep	17606285
[The contribution of capsular distension to the treatment of primary adhesive capsulitis of the shoulder: a comparative study versus rehabilitation].	2008 Dec	18926581
[Evaluation of the efficacy of CT-guided epidural and transforaminal steroid injections in patients with diskogenic radiculopathy].	2008 Jun	18641564
Circumvention of glucocorticoid resistance in childhood leukemia.	2008 Sep	18395253
Effectiveness of radiation synovectomy with samarium-153 particulate hydroxyapatite in rheumatoid arthritis patients with knee synovitis: a controlled randomized double-blind trial.	2009	20037706
Four cases of coccygeal disk calcification after cortivazol injection.	2009 Dec	19945326
Ligand-based gene expression profiling reveals novel roles of glucocorticoid receptor in cardiac metabolism.	2009 Jun	19293335
Injection therapy and denervation procedures for chronic low-back pain: a systematic review.	2010 Sep	20424870

Patents

Sample Use Guides

In Vivo Use Guide

300 ugrams of cortivazol is equivalent in anti-inflammatory activity to about 5 mg of prednisolone. It is given in the treatment of musculoskeletal and joint disorders by intra-articular, periarticular, or epidural injection in doses of about 1.25 to 3.75 mg, usually at intervals of 1 to 3 weeks.

Route of Administration: Other

In Vitro Use Guide

Incubation of ICR 27 cells with cortivazol caused 50% growth inhibition and 50% maximal induction of glutamine synthetase activity at concentrations of 20 and 35 nM, respectively.

Name

Type

Language

CORTIVAZOL

Official Name

English

CORTIVAZOL [MART.]

Common Name

English

CORTIVAZOL [MI]

Common Name

English

CORTIVAZOL [USAN]

Common Name

English

2'H-PREGNA-2,4,6-TRIENO(3,2-C)PYRAZOL-20-ONE, 21-(ACETYLOXY)-11,17-DIHYDROXY-6,16-DIMETHYL-2'-PHENYL-, (11.BETA.,16.ALPHA.)-

Common Name

English

11.BETA.,17,21-TRIHYDROXY-6,16.ALPHA.-DIMETHYL-2'-PHENYL-2'H-PREGNA-2,4,6-TRIENO(3,2-C)PYRAZOL-20-ONE 21-ACETATE

Common Name

English

NSC-80998

Code

English

cortivazol [INN]

Common Name

English

Cortivazol [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C521