DT-Web

DB00600 - Monobenzone


Identification
Name Monobenzone
Accession Number DB00600 (APRD01121)
Type small molecule
Description Monobenzone is the monobenzyl ether of hydroquinone used medically for depigmentation. Monobenzone occurs as a white, almost tasteless crystalline powder, soluble in alcohol and practically insoluble in water. The topical application of monobenzone in animals increases the excretion of melanin from the melanocytes. The same action is thought to be responsible for the depigmenting effect of the drug in humans. Monobenzone may cause destruction of melanocytes and permanent depigmentation.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 200.2332
Groups approved
Monoisotopic Weight 200.083729628
Pharmacology
Indication Used topically to treat the loss of skin color (vitiligo).
Mechanism of action Monobenzone is a depigmenting agent whose mechanism of action is not fully understood. The topical application of monobenzone in animals, increases the excretion of melanin from the melanocytes. The same action is thought to be responsible for the depigmenting effect of the drug in humans. Monobenzone may cause destruction of melanocytes and permanent depigmentation. This effect is erratic and may take one to four months to occur while existing melanin is lost with normal sloughing of the stratum corneum. Hyperpigmented skin appears to fade more rapidly than does normal skin, and exposure to sunlight reduces the depigmenting effect of the drug. The histology of the skin after depigmentation with topical monobenzone is the same as that seen in vitiligo; the epidermis is normal except for the absence of identifiable melanocytes.
Absorption Not Available
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Tyrosinase
Name Tyrosinase
Gene Name TYR
Pharmacological action unknown
Actions inhibitor
References
  • Chen YR, Y-Y R, Lin TY, Huang CP, Tang WC, Chen ST, Lin SB: Identification of an Alkylhydroquinone from Rhus succedanea as an Inhibitor of Tyrosinase and Melanogenesis. J Agric Food Chem. 2009 Mar 25;57(6):2200-5. - Pubmed
DTHybrid score 0.5836

Predictions


Id Partner name Gene Name Score
1649 Small inducible cytokine A2 CCL2 0.11
367 Serine hydroxymethyltransferase, cytosolic SHMT1 0.0828
526 Thioredoxin reductase trxB 0.0798
3767 Thioredoxin reductase trxB 0.0798
553 DNA polymerase I polA 0.0664
6373 DNA polymerase I polA 0.0664
642 3-oxo-5-alpha-steroid 4-dehydrogenase 2 SRD5A2 0.0576
6105 3-oxo-5-beta-steroid 4-dehydrogenase AKR1D1 0.0531
816 Biliverdin reductase A BLVRA 0.0028
579 Alcohol dehydrogenase class 4 mu/sigma chain ADH7 0.0028
792 Aldehyde dehydrogenase, dimeric NADP-preferring ALDH3A1 0.0028
316 4-trimethylaminobutyraldehyde dehydrogenase ALDH9A1 0.0028
247 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 1 NDUFA1 0.0027
343 NADH dehydrogenase [ubiquinone] 1 subunit C1, mitochondrial NDUFC1 0.0027
568 NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 7 NDUFB7 0.0027
313 NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 3 NDUFB3 0.0027
300 NADH-ubiquinone oxidoreductase chain 4L MT-ND4L 0.0027
374 NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 1 NDUFB1 0.0027
475 NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 2, mitochondrial NDUFB2 0.0027
99 NADH dehydrogenase [ubiquinone] iron-sulfur protein 5 NDUFS5 0.0027
755 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 3 NDUFA3 0.0027
598 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 11 NDUFA11 0.0027
324 NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 4 NDUFB4 0.0027
190 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 4 NDUFA4 0.0027
829 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 12 NDUFA12 0.0027
353 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 4-like 2 NDUFA4L2 0.0027
602 Acyl carrier protein, mitochondrial NDUFAB1 0.0027
272 NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 10 NDUFB10 0.0027
384 NADH-ubiquinone oxidoreductase chain 6 MT-ND6 0.0027
607 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 2 NDUFA2 0.0027
555 NADH dehydrogenase [ubiquinone] iron-sulfur protein 4, mitochondrial NDUFS4 0.0027
656 NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 9 NDUFB9 0.0027
270 NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 5, mitochondrial NDUFB5 0.0027
30 NADH dehydrogenase [ubiquinone] flavoprotein 3, mitochondrial NDUFV3 0.0027
446 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 7 NDUFA7 0.0027
525 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 5 NDUFA5 0.0027
219 NADH-ubiquinone oxidoreductase chain 3 MT-ND3 0.0027
729 GDP-L-fucose synthetase TSTA3 0.0027
3463 GDP-L-fucose synthetase fcl 0.0027
141 3-hydroxyisobutyrate dehydrogenase, mitochondrial HIBADH 0.0027
405 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 8 NDUFA8 0.0027
104 NADH dehydrogenase [ubiquinone] iron-sulfur protein 6, mitochondrial NDUFS6 0.0027
236 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 6 NDUFA6 0.0027
417 NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 6 NDUFB6 0.0027
335 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 9, mitochondrial NDUFA9 0.0027
582 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 13 NDUFA13 0.0027
145 Corticosteroid 11-beta-dehydrogenase isozyme 2 HSD11B2 0.0027
609 15-hydroxyprostaglandin dehydrogenase [NAD+] HPGD 0.0027
107 C-4 methylsterol oxidase SC4MOL 0.0027
372 Estradiol 17-beta-dehydrogenase 3 HSD17B3 0.0027
152 NADH dehydrogenase [ubiquinone] flavoprotein 2, mitochondrial NDUFV2 0.0027
487 Aldo-keto reductase family 1 member C4 AKR1C4 0.0027
746 NADH dehydrogenase [ubiquinone] 1 beta subcomplex subunit 8, mitochondrial NDUFB8 0.0027
326 L-lactate dehydrogenase A-like 6A LDHAL6A 0.0027
206 3-keto-steroid reductase HSD17B7 0.0027
196 D-beta-hydroxybutyrate dehydrogenase, mitochondrial BDH1 0.0027
721 NADH-ubiquinone oxidoreductase chain 2 MT-ND2 0.0027
91 NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 10, mitochondrial NDUFA10 0.0027
271 Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial ALDH4A1 0.0027
14 Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial IDH3A 0.0027
50 Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating NSDHL 0.0027
41 NADH dehydrogenase [ubiquinone] iron-sulfur protein 8, mitochondrial NDUFS8 0.0027
112 L-lactate dehydrogenase A-like 6B LDHAL6B 0.0027
216 Aldehyde dehydrogenase 3B2 ALDH3B2 0.0027
616 Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial IDH3B 0.0027
9 Estradiol 17-beta-dehydrogenase 2 HSD17B2 0.0027
628 Pyruvate dehydrogenase E1 component alpha subunit, somatic form, mitochondrial PDHA1 0.0027
848 Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrial IDH3G 0.0027
644 Heme oxygenase 2 HMOX2 0.0027
4982 Heme oxygenase 2 pbsA2 0.0027
180 D-3-phosphoglycerate dehydrogenase PHGDH 0.0027
3726 D-3-phosphoglycerate dehydrogenase serA 0.0027
4291 D-3-phosphoglycerate dehydrogenase serA 0.0027
608 NADH-ubiquinone oxidoreductase chain 4 MT-ND4 0.0027
539 NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial NDUFV1 0.0027
496 Aldehyde dehydrogenase 3B1 ALDH3B1 0.0027
34 7-dehydrocholesterol reductase DHCR7 0.0027
662 Fatty aldehyde dehydrogenase ALDH3A2 0.0027
711 UDP-glucose 6-dehydrogenase UGDH 0.0027
3672 UDP-glucose 6-dehydrogenase hasB 0.0027
149 Alpha-aminoadipic semialdehyde dehydrogenase ALDH7A1 0.0027
258 Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial ALDH6A1 0.0027
167 L-lactate dehydrogenase C chain LDHC 0.0027
637 NADH-ubiquinone oxidoreductase chain 5 MT-ND5 0.0027
231 Glycerol-3-phosphate dehydrogenase [NAD+], cytoplasmic GPD1 0.0027
531 Aldehyde dehydrogenase X, mitochondrial ALDH1B1 0.0027
671 Pyruvate dehydrogenase E1 component alpha subunit, testis-specific form, mitochondrial PDHA2 0.0027
643 Peroxisomal bifunctional enzyme EHHADH 0.0027
548 NADH-ubiquinone oxidoreductase 75 kDa subunit, mitochondrial NDUFS1 0.0027
288 Trifunctional enzyme subunit alpha, mitochondrial HADHA 0.0027
393 GDH/6PGL endoplasmic bifunctional protein [Includes: Glucose 1-dehydrogenase H6PD 0.0027
646 Malate dehydrogenase, cytoplasmic MDH1 0.0024
350 3-hydroxyacyl-CoA dehydrogenase type-2 HSD17B10 0.0024
178 NADH-cytochrome b5 reductase 3 CYB5R3 0.0024
812 Dihydrolipoyl dehydrogenase, mitochondrial DLD 0.0024
830 Glutamate dehydrogenase 2, mitochondrial GLUD2 0.0024
454 Peroxisomal multifunctional enzyme type 2 HSD17B4 0.0024
363 NADP-dependent malic enzyme, mitochondrial ME3 0.0024
328 Sorbitol dehydrogenase SORD 0.0023
597 Dihydropteridine reductase QDPR 0.0023
396 Alcohol dehydrogenase 4 ADH4 0.0023
635 Estradiol 17-beta-dehydrogenase 8 HSD17B8 0.0023
666 NADP-dependent malic enzyme ME1 0.0023
248 Pyrroline-5-carboxylate reductase 1 PYCR1 0.0022
802 Pyrroline-5-carboxylate reductase 2 PYCR2 0.0022
626 Cysteine dioxygenase type 1 CDO1 0.0022
296 Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial MTHFD2 0.0022
857 Malate dehydrogenase, mitochondrial MDH2 0.0022
194 NADH dehydrogenase [ubiquinone] 1 subunit C2 NDUFC2 0.0022
6026 Alcohol dehydrogenase 6 ADH6 0.0022
182 2-oxoglutarate dehydrogenase E1 component, mitochondrial OGDH 0.0022
110 Pyruvate dehydrogenase E1 component subunit beta, mitochondrial PDHB 0.0022
337 NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial NDUFS7 0.0022
214 NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial NDUFS3 0.0022
803 NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial NDUFS2 0.0022
419 Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial HADH 0.0021
12 Alcohol dehydrogenase class 3 ADH5 0.0021
627 11-cis retinol dehydrogenase RDH5 0.0021
640 Aldehyde dehydrogenase 1A3 ALDH1A3 0.0021
77 L-lactate dehydrogenase B chain LDHB 0.0021
569 Retinal dehydrogenase 2 ALDH1A2 0.0021
66 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type II HSD3B2 0.0021
11 NAD(P) transhydrogenase, mitochondrial NNT 0.0021
201 Glutamate dehydrogenase 1, mitochondrial GLUD1 0.002
839 Short-chain specific acyl-CoA dehydrogenase, mitochondrial ACADS 0.002
599 Glyceraldehyde-3-phosphate dehydrogenase GAPDH 0.002
4426 Glyceraldehyde-3-phosphate dehydrogenase gap 0.002
4454 Glyceraldehyde-3-phosphate dehydrogenase gap 0.002
4489 Glyceraldehyde-3-phosphate dehydrogenase gap 0.002
13 Aminomethyltransferase, mitochondrial AMT 0.002
74 Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrial DLAT 0.002
6861 Alcohol dehydrogenase [NADP+] AKR1A1 0.002
473 L-lactate dehydrogenase A chain LDHA 0.002
794 Glyceraldehyde-3-phosphate dehydrogenase, testis-specific GAPDHS 0.002
611 Retinal dehydrogenase 1 ALDH1A1 0.0019
57 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type I HSD3B1 0.0019
83 Alpha-aminoadipic semialdehyde synthase, mitochondrial AASS 0.0019
686 Aldo-keto reductase family 1 member C2 AKR1C2 0.0019
166 NAD-dependent malic enzyme, mitochondrial ME2 0.0019
170 Succinate semialdehyde dehydrogenase, mitochondrial ALDH5A1 0.0018
251 Alcohol dehydrogenase 1A ADH1A 0.0018
679 C-1-tetrahydrofolate synthase, cytoplasmic MTHFD1 0.0018
838 Inosine-5'-monophosphate dehydrogenase 1 IMPDH1 0.0018
796 Inosine-5'-monophosphate dehydrogenase 2 IMPDH2 0.0017
139 Aldo-keto reductase family 1 member C1 AKR1C1 0.0017
654 Flavin reductase BLVRB 0.0017
217 Estradiol 17-beta-dehydrogenase 1 HSD17B1 0.0016
810 Heme oxygenase 1 HMOX1 0.0016
3391 Heme oxygenase 1 pbsA1 0.0016
444 Alcohol dehydrogenase 1B ADH1B 0.0016
147 Aldehyde dehydrogenase, mitochondrial ALDH2 0.0016
380 Cytochrome P450 17A1 CYP17A1 0.0016
650 Aldo-keto reductase family 1 member C3 AKR1C3 0.0015
559 NADH-ubiquinone oxidoreductase chain 1 MT-ND1 0.0015
468 Cytochrome P450 4A11 CYP4A11 0.0015
714 Glutathione reductase, mitochondrial GSR 0.0015
631 3-hydroxy-3-methylglutaryl-coenzyme A reductase HMGCR 0.0015
3387 3-hydroxy-3-methylglutaryl-coenzyme A reductase mvaA 0.0015
243 Ribosyldihydronicotinamide dehydrogenase [quinone] NQO2 0.0015
6020 Aldehyde oxidase AOX1 0.0014
517 Alcohol dehydrogenase 1C ADH1C 0.0014
364 Corticosteroid 11-beta-dehydrogenase isozyme 1 HSD11B1 0.0013
3947 Xanthine dehydrogenase/oxidase XDH 0.0013
365 Dihydrofolate reductase DHFR 0.0012
2381 Dihydrofolate reductase DFR1 0.0012
2833 Dihydrofolate reductase Not Available 0.0012
2931 Dihydrofolate reductase folA 0.0012
3544 Dihydrofolate reductase folA 0.0012
3682 Dihydrofolate reductase folA 0.0012
6642 Dihydrofolate reductase folA 0.0012
6756 Dihydrofolate reductase dfrA 0.0012
822 Aldose reductase AKR1B1 0.0012
↑