KEGG   ENZYME: 1.14.14.73
Entry
EC 1.14.14.73               Enzyme                                 
Name
albendazole monooxygenase (sulfoxide-forming);
albendazole sulfoxidase (ambiguous);
albendazole hydroxylase (ambiguous);
CYP3A4 (gene name);
CYP2J2 (gene name);
CYP1A2 (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
albendazole,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (sulfoxide-forming)
Reaction(IUBMB)
(1) albendazole + [reduced NADPH---hemoprotein reductase] + O2 = albendazole S-oxide + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R12068];
(2) fenbendazole + [reduced NADPH---hemoprotein reductase] + O2 = fenbendazole S-oxide + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R12069]
Reaction(KEGG)
R12068 R12069
Substrate
albendazole [CPD:C01779];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
fenbendazole [CPD:C21876]
Product
albendazole S-oxide [CPD:C02809];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
fenbendazole S-oxide [CPD:C21882]
Comment
This is one of the activities carried out by some microsomal cytochrome P-450 monooxygenases. A similar conversion is also carried out by a different microsomal enzyme (EC 1.14.13.32, albendazole monooxygenase (flavin-containing)), but it is estimated that cytochrome P-450s are responsible for 70% of the activity.
History
EC 1.14.14.73 created 2018
Orthology
K07418  cytochrome P450 family 2 subfamily J
K17689  cytochrome P450 family 3 subfamily A4
Genes
HSA1573(CYP2J2) 1576(CYP3A4)
PTR456896(CYP2J2) 463582(CYP3A4)
PPS100976899(CYP3A4) 100984148(CYP2J2)
GGO101148349 101149513
PON100436782 100447634
PPYG129016979 129041698
NLE100589053 100593175
HMH116457699
SSYN129458528 129489604
MCC678670(CYP3A4) 693631
MCF102119662(CYP2J2) 102144258(CYP3A4)
MTHB126950475 126962785
MNI105495154 105497389
CSAB103224719(CYP2J2) 103246766
CATY105584402 105595967
PANU101015175 101026757 116276324 116276330
TGE112621193 112630798
MLEU105534929 105543708
RRO104668045 104673585
RBB108532916 108538168
TFN117072034 117091994
PTEH111522986 111530171 111534893
CANG105511111 105513064
CJC100397287(CYP2J2) 100404344(CYP3A4)
SBQ101037403 101041470
CIMI108308036(CYP3A4) 108314910(CYP2J2)
ANAN105710194(CYP2J2) 105719456(CYP3A4)
CSYR103252931 103256114
MMUR105868328 105868331 105882593 105882595 105882596
LCAT123631591 123631593 123635586 123635587 123635588
PCOQ105806078 105806372 105806374
OGA100948865 100950432 100950736 100951049 100951361
MMU100066(Cyp2j11) 13109(Cyp2j5) 13110(Cyp2j6) 230459(Cyp2j13) 242546(Cyp2j12) 546837(Cyp2j7) 665095(Cyp2j8) 74519(Cyp2j9)
MCAL110292385 110292662 110292766 110293055 110293363 110293364 110306650
MPAH110323111 110323251 110323340 110323372 110323386 110323498
RNO100912642 313373(Cyp2j10) 313375(Cyp2j3) 502969(Cyp2j16) 65210(Cyp2j4)
MCOC116095445 116095729 116095730 116096253 116096254 116096255 116096256
ANU117709291 117709292 117709294 117709295 117709296 117709297 117709298 117709299
MUN110560670 110560674 110560675 110562464 110562465 110562466 110562514
CGE100764171 100764471 100764768 100765057
MAUA101830438 101830700 101841191 101841462
PROB127224955 127224956 127224957 127224959
PLEU114681971 114681974 114681989 114681994 114689366 114693759 114693760 114693761 114693762 114693764
MORG121448178 121448207 121448212 121448217 121448239 121448362 121448363 121448623 121448757 121448759 121448836 121448885
MFOT126498042 126498043 126498046 126498047 126498076 126498100 126508049
AAMP119816658 119816659 119816660 119816661 119816663 119816664 119816666 119816978
NGI103730878 103730879 103730880 103737136
HGL101719021 101719368
CCAN109684284
DORD105989978 105990009
DSP122108987 122111431
PLOP125355228 125355229
NCAR124966849
MMMA107141706
OCU100301544(CYP2J1)
OPI101531357 101531516
TUP102490783 102491196 102491623 102492033 102492447
GVR103603536
CFA610195(CYP2J2)
CLUD112647122
VVP112926087
VLG121499260
NPO129497114
AML100482335
UMR103663082
UAH113254606
UAR123795371
ELK111143525
LLV125097704
MPUF101684683
MNP132000940
MLK131809515
NVS122900029
ORO101382939
EJU114212028
ZCA113926705
MLX118020215
NSU110571781
LWW102747983
FCA101097746(CYP2J2)
PYU121027220
PCOO112871803
PBG122480573
PVIV125173408
LRUF124516300
PTG102958105
PPAD109266776
PUC125912544
AJU106974984
HHV120236077
BTA107132327 510406(CYP2J30) 511936 521656 530929
BOM102283844 102284389
BIU109556228 109556861
BBUB102409898 102410549 102410893 102411225 102411786
BBIS105002568 105002577 105002593 105002602 105002609
CHX102184867 102190572 102190840 102191099
OAS101121563 101121820 768095(CYP2J)
BTAX128044628 128044629 128045187
ODA120856578 120857076 120857077 120857078 120857079
CCAD122436913 122436914 122436915 122436916
MBEZ129540345 129540908 129540938 129541372 129541501
SSC100524750(CYP2J34) 100524940 100525112 100621407 110261221
CFR102509190 102509309 102511878 102518893
CBAI105064824 105064834 105064844 105064851 105065015
CDK105092804 105092849 105096275 105096288
VPC102524867 102535306 102535561 102535809 102536059 102536560 102543101 102543350
BMUS118895900
LVE103072875
OOR101287985
DLE111175878
PCAD102995526
PSIU116764420
NASI112407074
ECB100067247
EPZ103564165
EAI106833456
MYB102259820
MYD102765527
MMYO118676695
MLF102439141
MDT132231009
PKL118723974 118723975
EFUS103284070
MNA107531748
AJM119042498
PDIC114496360 114496679 114497261 114497336
PHAS123816495 123830867 123831702
MMF118627182
PPAM129070802
HAI109371253 109389703 109389708
RFQ117026547 117026565 117027269
PALE102885276
PGIG120621913
PVP105303444
RAY107518358
TOD119236796 119236797
SARA101547147 101547409 101547677 101547951 101558147 101558420
SETR126010975 126010977 126010978 126010985 126010986 126011645
LAV100658115 100670142
TMU101350163
ETF101644960 101645270 101645590
DNM101411038 101437056 101438656 101439086 101439781 101440211 101440653 101447575
MDO100031902 100031907 100031914 100031960 100031971 100031975 100031980 100031984
GAS123243734 123245774 123245775 123245776 123247875 123247893
SHR100921692 100921949 100922209 100922468 100922742 100922989 116419008
AFZ127563232 127563233 127563234 127563235 127563236 127563237 127563238
PCW110212934 110212942 110212976 110212978
TVP118846138 118846140 118846141 118846143 118846144 118846152 118846466 118846467 118846468
OAA100087745
GGA101750603(CYP2J21) 424676(CYP2J23) 424677(CYP2J22) 424729(CYP2J19)
PCOC116235297 116236300 116236311
MGP100547794 104912427 104912428 104912494
CJO107317676 107317691 107317696
TPAI128072441 128072442 128072444 128072445 128072446 128072447
LMUT125692983 125693898 125693899
NMEL110402810 110402814
APLA101792912 101796247
CATA118243378 118243450
AFUL116491839 116491861
TGU100224220(CYP2J40) 100230439(CYP2J19A)
LSR110477035 110477061
SCAN103815060 103815209(CYP2J19)
PMOA120503273 120503274
OTC121345089 121345090
PRUF121362071 121362072
GFR102032779 102039653
FAB101811920 101817417
OMA130256010 130256011
PHI102099263 102112918
PMAJ107208256 107208257
CCAE111932992 111932994
CCW104695151 104695152
CBRC103615060 103615112
ETL114069063
ZAB102067922
ZLE135450762 135450763 135450766
ACHL103807106
SVG106849737 106849804
HRT120756468 120756532
SATI136365094 136365095
FPG101919387
CCRI104159712
SHAB115611484 115611485 115611814 115611815 115611982
ACUN113483076 113483077
TALA104356817 104369422 116964786 122152520
ACHC115349168 115349169
HALD104317809 104317810
AGEN126041970 126041971
GCL127018852 127019141
CSTI104561860 104561861
LDI104353037 104353038
MNB103769046 103769625 103776455 103779509 103780917
DPUB104301748 104301760 104308782
AVIT104278846
BRHI104488759
EGZ104123882 104123941
NNI104009259 104009336
PCRI104028699
PCAO104041925 104041927
PADL103913325 103913366
AFOR103905667 103905758
FGA104077513 104077514
GSTE104260318 104260319
CLV102088854 102089036 102093649 102094339
MUI104535857 104535919
PGUU104462916
PLET104623376 104623378
EHS104505453 104509239
CMAC104478964 104484601
CUCA104066545 104066584
TEO104371533 104377407 104382055
BREG104632733 104632734
OHA104328012 104328025
ACAR104520204
CPEA104385164 104385194
CVF104285547
RTD128913617 128913618
AROW112967651 112976566
NPD112942289 112948473 112948476 112948493
TGT104571164 104571376 104575346 104575680 104575681
DNE112991483 112991487
SCAM104152907 104153320
ASN102371261 102371780
AMJ102557714(CYP2P10)
CPOO109307018
GGN109305297
PSS102449417 102457302(CYP2J19) 102460777
CMY102936353 102940076(CYP2J19)
CCAY125640754 125640755
DCC119859977
CPIC101931915 101937882 101938148(CYP2J19) 101939779 103305685
TST117882110
CABI116833772
MRV120370576 120370577 120370720 120370721
ACS100567522
ASAO132772700 132772701 132772702 132773987
SUND121927978 121927980 121927981
VKO123018898 123019432 123019440 123019512 123025295 123025296 123025297 123025298 123025301
PMUA114598918 114598919 114598920 114598921 114598923 114598924 114598925
PRAF128410871 128410872 128410874 128410875 128410876 128410877 128410878 128415691 128415692 128415694 128415695 128415696 128415697 128415703
ZVI118088450 118088451 118088452 118088453 118088455 118088457
HCG128324567 128324673
GJA107111277 107114997
STOW125437750 125437751 125437990
EMC129329793
MUO115472051
GSH117346547
DRE100034366(cyp2p8) 100034406(cyp2p7) 393108(cyp2p6) 393592(cyp2p9) 399485(cyp2p10) 797309(cyp2j20)
SRX107737305
SANH107665313
SGH107556152 107556153
CCAR109081729 109112720 109112721 109112722
CAUA113059714 113062932 113062933 113062936 113077208
CGIB127939007 127939011 127939012 127944356 127944764 127956825
PTET122325384 122325385 122325386
LROH127163996 127182750 127182753 127182754 127182755
OMC131526777 131526778 131538917
PPRM120493435 120495341
RKG130070236 130091794
MAMB125271930 125277848 125277849 125277850 125277851 125277854 125277856
CIDE127502658
CERY137018370 137018936 137018939 137018940 137018941
MASI127415948
TROS130565655
TDW130434345
MANU129429259 129429260
AMEX103037239 125803022
CMAO118815408 118815409
EEE113568096 113586377
CHAR105900861 105900876
TRU101075700
TFS130529142
LCO104930795 104930796
CGOB115007060
PGEO117455593
GACU117556494
EMAC134864748
ELY117253502 117253503 117253504
EFO125895935 125895937 125895938
PLEP121939575 121939585
SLUC116063278
ECRA117950841
ESP116695040 116695044
PFLV114560939
PPUG119216714
AFB129094823
CLUM117729246
PSWI130194467
MSAM119900968 119900969 119900982 119901367
SCHU122878258
CUD121511981 121511983 121511984 121511985
ALAT119028085 119028086 119028087 119028088 119028090
MZE101469747 101471484 101471776 101472450 101472746 101473039 101473341 101473625 101474137 112429716 112430356 112430410
ONL100699361 100699634 100699898 100700165 100700439 100700441 100700978 100701255 100701799 109194408 109196838 109196840
OAU116315351 116327896 116327898 116331077 116331078 116331079 116331081 116331082 116331187 116331213 120436259 120436353
OLA100302452(cyp2p3) 105353996
OML112138317 112150360 112150361 112150362 118597890
CSAI133458178 133458179 133458180 133458188
XMA102216555 102216815 102224544 102235118 102238098 102238367
XCO114150919 114150920 114150922
XHE116725631 116725632 116725633 116725634 116725636 116725637 116725638 116725642 116725644
PRET103461257 103463736 103463738 103463739
PFOR103137021 103137022 103137164 103137165
PLAI106949663 106949692 106949693 106949694 106961243 106961249
PMEI106908422 106908423 106917754 106917779 106917780
GAF122838407 122838408 122838409 122838410 122838411
PPRL129377269 129377278 129377282 129377290
CVG107095777 107099581
CTUL119777086 119790019 119790034
GMU124873252 124873920
NFU107395372 107395373
KMR108230681 108230682 108230683 108230684 108230685
ALIM106517296 106517297 106517298
NWH119421487 119430737
AOCE111563453 111564682 111564718 111564989 111564993 111586280 111586281 111586282
MCEP125009824 125009825 125009826 125009827 125009828 125009830 125009831 125009832 125009834
CSEM103383190
POV109625616
SSEN122777824 122777825
HSP118121284
LCF108879066 108879067
SDU111232055 111232106
SLAL111653766 111656353
BPEC110173990
BSPL114852938 114853161 114853162 114853163 114854720 114854721 114854722 114854723
SASA106584062
STRU115157896 115192271
OTW112250281
OMY110521776
OGO124038052
ONE115145370
OKI109898106
OKE118358831
SALP111971193
SNH120052641
CCLU121533858
ELS105025359
SFM108923501 108923503 108927875 108934003 108935367 108935464 114909092 114911247 114911248 114911249 114911250 114911251 114911252 114911257 114911278
PKI111834855 111834857 111834858 111834859
AANG118224796 118224797 118224802
PSPA121327058 121330919
ARUT117409945 117409954 117417241 117417316
PSEX120514266 120514351 120514536 120514588 120514690 120514765
CMK103185273
RTP109921744
LERI129700975
PMRN116942349 116949610
LRJ133347001 133347343
BFO118405297 118407101 118419304 118428418 118429635 118432366
BBEL109461524 109461651 109461725 109461727 109462264 109465453 109465656 109466367 109467919 109471284 109472128 109472267 109472270 109475266 109477936 109480295 109482013 109482167 109483920 109483935 109483947 109483948 109485002
SCLV120333811 120334172 120334246 120343352
LPIC129255057 129255413 129259914 129260274 129261294 129263280 129267050 129267667 129272440 129272952 129272957 129273267 129274630 129276166 129276247 129281166 129281317 129281383 129281480 129281481 129281482 129281553 129282251
ARUN117287782 117288024 117288160 117288161 117288273 117288601 117289770 117294724 117298615 117299860 117299861 117301387 117303760 117304080 117304753 117304847 117304890 117305170 117307185
AJC117111890 117111891
BCOO119083310
PVM113807691
PJA122242547 122243682 122252347 122252348 122259834 122259836 122260679 122263851
PCHN125037284 125037285 125037286 125037288 125037553 125040652 125047318 125047985
HAME121853159 121857091 121874841
PCLA123746738 123751553 123756377 123767033 123767752 123770238 123770240
CQD128685195 128686126 128686746 128693801 128694775 128697090 128703751 128704994
PTRU123506617 123506674
ESN126984741 126987539 126992673
MNZ135202400 135214473 135220037 135223714
MRJ136828209 136834865 136847066 136848421 136848600 136855122
HAZT108665745 108667157 108667158 108674876 108676835
EAF111695177 111696904 111696905 111698334 111704925 111704939 111706377 111709242 111713706 111717082 111717477 111718077
LSM121115047 121119889 121121717
TCF131880430 131880431 131881008 131883247 131884276 131893305
PPOI119091992 119095707 119101079 119101087 119101104 119101111 119101120 119101130 119104411 119109569
DSV119441628 119457522 119461188 119461547 119462117
RSAN119374231 119383506 119383507 119386647 119390617 119397387 119406751
RMP119166963 119169660 119171404 119173720
VDE111244479
VJA111272117
CVS136969341 136972707
ABRU129957692 129964081 129964121 129968576 129968577 129972410 129972618 129973475 129973840 129980922
UDV129220639 129220886 129229762 129233369 129234350
SDM118180345 118189454 118190843 118190848 118202040 118203101 118206070
LPOL106459164 106475453
PMEO129583244 129584069 129586991 129587294 129588909 129588911 129590632 129591781 129596265 129598004 129599617 129599629 129599630 129600908 129600978 129600979 129600986
PVUL126809973 126810313 126811410 126811411 126811412 126811413 126811418 126825321 126832216
BGT106054491 106054493 106055467 106057592 106057638 106059997 106060000 106070555 106074975
GAE121374745 121382078
HRF124113283 124118458 124118459 124140343 124140344 124144343 124144711 124147838 124147839 124147840 124152329
HRJ124261308 124267336 124267348 124279341 124281198 124281746 124290622 124290663 124291032 124291033 124291034
CRG105329932 105332463 117689293
CANU128155298 128176608 128181027 128188649
CVN111108895 111110523 111110669 111122683 111123229 111128037 111132556
OED125650159 125650617 125651484 125651530 125652691 125652692 125652694 125652695 125654191 125656391 125681271 125683308 130046407 130054718
PMAX117316069 117343471
MCAF127723994
MMER123543547 123558935
RPHI132718487 132725871 132732507 132737309 132749504
DPOL127856874 127856875 127866967 127866970 127872507
MAEA128209932 128232792 128233722
OSN115217140 115217142 115220404 115224293 115227007 115232209
LJP135476777 135481015
LLON135489098 135494781 135498002 135500702 135503101
XEN124445682
 » show all
Reference
1  [PMID:7736906]
  Authors
Moroni P, Buronfosse T, Longin-Sauvageon C, Delatour P, Benoit E
  Title
Chiral sulfoxidation of albendazole by the flavin adenine dinucleotide-containing and cytochrome P450-dependent monooxygenases from rat liver microsomes.
  Journal
Drug Metab Dispos 23:160-5 (1995)
Reference
2  [PMID:10759686]
  Authors
Rawden HC, Kokwaro GO, Ward SA, Edwards G.
  Title
Relative contribution of cytochromes P-450 and flavin-containing monoxygenases to the metabolism of albendazole by human liver microsomes.
  Journal
Br J Clin Pharmacol 49:313-22 (2000)
DOI:10.1046/j.1365-2125.2000.00170.x
Reference
3  [PMID:11137466]
  Authors
Asteinza J, Camacho-Carranza R, Reyes-Reyes RE, Dorado-Gonzalez V V, Espinosa-Aguirre JJ
  Title
Induction of cytochrome P450 enzymes by albendazole treatment in the rat.
  Journal
Environ Toxicol Pharmacol 9:31-37 (2000)
DOI:10.1016/S1382-6689(00)00059-4
Reference
4  [PMID:19923256]
  Authors
Lee CA, Neul D, Clouser-Roche A, Dalvie D, Wester MR, Jiang Y, Jones JP 3rd, Freiwald S, Zientek M, Totah RA.
  Title
Identification of novel substrates for human cytochrome P450 2J2.
  Journal
Drug Metab Dispos 38:347-56 (2010)
DOI:10.1124/dmd.109.030270
  Sequence
[hsa:1573]
Reference
5  [PMID:23959307]
  Authors
Wu Z, Lee D, Joo J, Shin JH, Kang W, Oh S, Lee DY, Lee SJ, Yea SS, Lee HS, Lee T, Liu KH
  Title
CYP2J2 and CYP2C19 are the major enzymes responsible for metabolism of albendazole and fenbendazole in human liver microsomes and recombinant P450 assay systems.
  Journal
Antimicrob Agents Chemother 57:5448-56 (2013)
DOI:10.1128/AAC.00843-13
  Sequence
[hsa:1573]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.73
IUBMB Enzyme Nomenclature: 1.14.14.73
ExPASy - ENZYME nomenclature database: 1.14.14.73
BRENDA, the Enzyme Database: 1.14.14.73
CAS: 9059-22-7
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