CYP24, CYP26 and CYP27 families | Enzymes | IUPHAR/BPS Guide to PHARMACOLOGY

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CYP24, CYP26 and CYP27 families

CYP24, CYP26 and CYP27 families C

Unless otherwise stated all data on this page refer to the human proteins. Gene information is provided for human (Hs), mouse (Mm) and rat (Rn).

Overview

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CYP24s deactivate vitamin D metabolites and CYP27s are required for the biosynthesis of vitamin D from cholesterol. CYP26 enzymes metabolise excess all-trans-retinol to limit toxicity.

Enzymes

Vitamin D3 24-hydroxylase (CYP24A1) C Show summary »« Hide summary

Target Id

1365

Nomenclature

CYP24A1

Common abbreviation

Vitamin D3 24-hydroxylase

Previous and unofficial names

Genes

CYP24A1 (Hs), Cyp24a1 (Mm), Cyp24a1 (Rn)

Ensembl ID

ENSG00000019186 (Hs), ENSMUSG00000038567 (Mm), ENSRNOG00000013062 (Rn)

UniProtKB AC

Q07973 (Hs), Q64441 (Mm), Q09128 (Rn)

EC number

1.14.15.16

Inhibitors

CTA091 pIC₅₀ 8.2 [5]

lunacalcipol pIC₅₀ 7.6 [5]

compound 4d [PMID: 20655626] pIC₅₀ 4.8 [1]

Comment

Converts 1,25-dihydroxyvitamin D3 (calcitriol) to 1α,24R,25-trihydroxyvitamin D₃.

CYP26A1 C Show summary »« Hide summary More detailed page go icon to follow link

Target Id

1366

Nomenclature

CYP26A1

Previous and unofficial names

Genes

CYP26A1 (Hs), Cyp26a1 (Mm), Cyp26a1 (Rn)

Ensembl ID

ENSG00000095596 (Hs), ENSMUSG00000024987 (Mm), ENSRNOG00000016750 (Rn)

UniProtKB AC

O43174 (Hs), O55127 (Mm)

EC number

1.14.-.-

Inhibitors

R116010 pIC₅₀ 8.4 [7]

liarozole pIC₅₀ 5.7 [7]

talarozole [7]

Selective inhibitors

compound 5 [PMID: 21838328] pIC₅₀ 9.5 [2]

Comment

Converts retinoic acid to 4-hydroxyretinoic acid. Inhibited by liarozole

CYP26B1 C Show summary »« Hide summary

Target Id

1367

Nomenclature

CYP26B1

Previous and unofficial names

Retinoic acid-metabolizing cytochrome | cytochrome P450 26B1 | cytochrome P450, family 26, subfamily B, polypeptide 1 | cytochrome P450

Genes

CYP26B1 (Hs), Cyp26b1 (Mm), Cyp26b1 (Rn)

Ensembl ID

ENSG00000003137 (Hs), ENSMUSG00000063415 (Mm), ENSRNOG00000015076 (Rn)

UniProtKB AC

Q9NR63 (Hs), Q811W2 (Mm), G3V7X8 (Rn)

EC number

1.14.-.-

Comment

Converts retinoic acid to 4-hydroxyretinoic acid.

CYP26C1 C Show summary »« Hide summary

Target Id

1368

Nomenclature

CYP26C1

Previous and unofficial names

cytochrome P450 | cytochrome P450, family 26, subfamily c, polypeptide 1

Genes

CYP26C1 (Hs), Cyp26c1 (Mm), Cyp26c1 (Rn)

Ensembl ID

ENSG00000187553 (Hs), ENSMUSG00000062432 (Mm), ENSRNOG00000030698 (Rn)

UniProtKB AC

Q6V0L0 (Hs)

EC number

1.14.-.-

Comment

Converts retinoic acid to 4-hydroxyretinoic acid [6].

Sterol 27-hydroxylase (CYP27A1) C Show summary »« Hide summary

Target Id

1369

Nomenclature

CYP27A1

Common abbreviation

Sterol 27-hydroxylase

Previous and unofficial names

Genes

CYP27A1 (Hs), Cyp27a1 (Mm), Cyp27a1 (Rn)

Ensembl ID

ENSG00000135929 (Hs), ENSMUSG00000026170 (Mm), ENSRNOG00000017188 (Rn)

UniProtKB AC

Q02318 (Hs), Q9DBG1 (Mm), P17178 (Rn)

EC number

1.14.15.15

Inhibitors

compound 4d [PMID: 20655626] pIC₅₀ 7.2 [1]

CTA091 pIC₅₀ <6.0 [3]

Comment

Converts cholesterol to 27-hydroxycholesterol.

25-Hydroxyvitamin D 1-alpha-hydroxylase (CYP27B1) C Show summary »« Hide summary

Target Id

1370

Nomenclature

CYP27B1

Common abbreviation

25-Hydroxyvitamin D 1-alpha-hydroxylase

Previous and unofficial names

calcidiol 1-monooxygenase | VD3 1A hydroxylase | cytochrome P450 40 (25-hydroxyvitamin D3 1 alpha-hydroxylase) | cytochrome P450, family 27, subfamily B, polypeptide 1 | cytochrome P450

Genes

CYP27B1 (Hs), Cyp27b1 (Mm), Cyp27b1 (Rn)

Ensembl ID

ENSG00000111012 (Hs), ENSMUSG00000006724 (Mm), ENSRNOG00000046214 (Rn)

UniProtKB AC

O15528 (Hs), O35084 (Mm), O35132 (Rn)

EC number

1.14.15.18

Inhibitors

CTA091 pIC₅₀ 6.3 [3]

Comment

Converts 25-hydroxyvitamin D₃ to 1,25-dihydroxyvitamin D3 (calcitriol)

CYP27C1 C Show summary »« Hide summary

Target Id

1371

Nomenclature

CYP27C1

Previous and unofficial names

cytochrome P450, family 27, subfamily C, polypeptide 1

Genes

CYP27C1 (Hs)

Ensembl ID

ENSG00000186684 (Hs)

UniProtKB AC

Q4G0S4 (Hs)

EC number

1.14.19.53

Comment

Converts retinol (vitamin A1) to 3,4-didehydroretinol (vitamin A2) [4].

References

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1. Aboraia AS, Makowski B, Bahja A, Prosser D, Brancale A, Jones G, Simons C. (2010) Synthesis and CYP24A1 inhibitory activity of (E)-2-(2-substituted benzylidene)- and 2-(2-substituted benzyl)-6-methoxy-tetralones. Eur J Med Chem, 45 (10): 4427-34. [PMID:20655626]

2. Gomaa MS, Bridgens CE, Veal GJ, Redfern CP, Brancale A, Armstrong JL, Simons C. (2011) Synthesis and biological evaluation of 3-(1H-imidazol- and triazol-1-yl)-2,2-dimethyl-3-[4-(naphthalen-2-ylamino)phenyl]propyl derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26). J Med Chem, 54 (19): 6803-11. [PMID:21838328]

3. Kahraman M, Sinishtaj S, Dolan PM, Kensler TW, Peleg S, Saha U, Chuang SS, Bernstein G, Korczak B, Posner GH. (2004) Potent, selective and low-calcemic inhibitors of CYP24 hydroxylase: 24-sulfoximine analogues of the hormone 1alpha,25-dihydroxyvitamin D(3). J Med Chem, 47 (27): 6854-63. [PMID:15615534]

4. Kramlinger VM, Nagy LD, Fujiwara R, Johnson KM, Phan TT, Xiao Y, Enright JM, Toomey MB, Corbo JC, Guengerich FP. (2016) Human cytochrome P450 27C1 catalyzes 3,4-desaturation of retinoids. FEBS Lett, 590 (9): 1304-12. [PMID:27059013]

5. Posner GH, Helvig C, Cuerrier D, Collop D, Kharebov A, Ryder K, Epps T, Petkovich M. (2010) Vitamin D analogues targeting CYP24 in chronic kidney disease. J Steroid Biochem Mol Biol, 121 (1-2): 13-9. [PMID:20347976]

6. Taimi M, Helvig C, Wisniewski J, Ramshaw H, White J, Amad M, Korczak B, Petkovich M. (2004) A novel human cytochrome P450, CYP26C1, involved in metabolism of 9-cis and all-trans isomers of retinoic acid. J Biol Chem, 279 (1): 77-85. [PMID:14532297]

7. Thatcher JE, Buttrick B, Shaffer SA, Shimshoni JA, Goodlett DR, Nelson WL, Isoherranen N. (2011) Substrate specificity and ligand interactions of CYP26A1, the human liver retinoic acid hydroxylase. Mol Pharmacol, 80 (2): 228-39. [PMID:21521770]

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Concise Guide to PHARMACOLOGY citation:

Alexander SP, Fabbro D, Kelly E, Mathie A, Peters JA, Veale EL et al. (2021) THE CONCISE GUIDE TO PHARMACOLOGY 2021/22: Enzymes. Br J Pharmacol. 178 Suppl 1:S313-S411.