Human liver cocaine esterases: ethanol-mediated formation of ethylcocaine
A new, pharmacologically active metabolite of cocaine, ethylcocaine, has been reported in individuals after concurrent use of cocaine and ethanol. Formation of ethylcocaine may contribute to the common coabuse of these two drugs and the apparent danger of this practice. We have identified a nonspeci...
Saved in:
| Published in | The FASEB journal Vol. 5; no. 12; p. 2735 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
01.09.1991
|
| Subjects | |
| Online Access | Get more information |
Cover
Loading…
| Abstract | A new, pharmacologically active metabolite of cocaine, ethylcocaine, has been reported in individuals after concurrent use of cocaine and ethanol. Formation of ethylcocaine may contribute to the common coabuse of these two drugs and the apparent danger of this practice. We have identified a nonspecific carboxyl-esterase that catalyzes the ethyl transesterification of cocaine to ethylcocaine in the presence of ethanol. In the absence of ethanol, this human liver esterase catalyzes the hydrolysis of cocaine to benzoylecgonine, a metabolite that is inactive as a psychomotor stimulant. A second human liver esterase is also described. This enzyme catalyzes hydrolysis of cocaine to ecgonine methyl ester, also inactive as a stimulant. These two liver esterases may play important roles in regulating the metabolic inactivation of cocaine. |
|---|---|
| AbstractList | A new, pharmacologically active metabolite of cocaine, ethylcocaine, has been reported in individuals after concurrent use of cocaine and ethanol. Formation of ethylcocaine may contribute to the common coabuse of these two drugs and the apparent danger of this practice. We have identified a nonspecific carboxyl-esterase that catalyzes the ethyl transesterification of cocaine to ethylcocaine in the presence of ethanol. In the absence of ethanol, this human liver esterase catalyzes the hydrolysis of cocaine to benzoylecgonine, a metabolite that is inactive as a psychomotor stimulant. A second human liver esterase is also described. This enzyme catalyzes hydrolysis of cocaine to ecgonine methyl ester, also inactive as a stimulant. These two liver esterases may play important roles in regulating the metabolic inactivation of cocaine. |
| Author | Dean, R A Bosron, W F Christian, C D Sample, R H |
| Author_xml | – sequence: 1 givenname: R A surname: Dean fullname: Dean, R A organization: Department of Pathology, Indiana University School of Medicine, Indianapolis 46202-5122 – sequence: 2 givenname: C D surname: Christian fullname: Christian, C D – sequence: 3 givenname: R H surname: Sample fullname: Sample, R H – sequence: 4 givenname: W F surname: Bosron fullname: Bosron, W F |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/1916095$$D View this record in MEDLINE/PubMed |
| BookMark | eNotj81OwzAQhH0oKv3hCRCSXyBhvU4cmxuqgFaqxIWeK8dZi1SJXcUpUt-eInKaw8x8mlmyWYiBGHsUkAsw6tnbRPUpL3OBuTBCgSlnbAHaYKaU1PdsmdIJAAQINWfzKbJgu-2lt4F37Q8N3EVn20Cc0kjDDZheOI3fNsQu66lp7UgN93Ho7djGwKP_c6_d1FqzO2-7RA-Trtjh_e1rs832nx-7zes-c6VAldWEUEutkJQzugHj0TqnCywlVFVTeUTjFdiqUbowpKUBYQ15XwhfyULiij39c8-X-rbqeB7a3g7X43QJfwGdJU8u |
| CitedBy_id | crossref_primary_10_1016_0379_0738_95_01821_2 crossref_primary_10_1016_0378_4347_93_80080_N crossref_primary_10_1016_j_foodchem_2022_134307 crossref_primary_10_1016_S0006_8993_98_00714_8 crossref_primary_10_1002_hup_2592 crossref_primary_10_1002_prp2_1009 crossref_primary_10_1002__SICI_1096_9888_199906_34_6_651__AID_JMS817_3_0_CO_2_M crossref_primary_10_1074_jbc_272_23_14769 crossref_primary_10_1016_S0378_4347_98_00348_X crossref_primary_10_1177_0269881117711923 crossref_primary_10_1007_BF02245328 crossref_primary_10_1016_S0749_0704_05_70370_5 crossref_primary_10_1007_s00213_004_1996_2 crossref_primary_10_3109_00498254_2011_573016 crossref_primary_10_1111_j_1530_0277_2001_tb02319_x crossref_primary_10_1002_rcm_8747 crossref_primary_10_1016_j_apsb_2018_05_005 crossref_primary_10_1111_j_1521_0391_2009_00009_x crossref_primary_10_1016_S0163_7827_98_00013_7 crossref_primary_10_1081_CLT_120039540 crossref_primary_10_1016_0024_3205_96_00435_3 crossref_primary_10_1016_S0091_3057_97_00476_0 crossref_primary_10_1080_13556219971498 crossref_primary_10_1124_dmd_111_041335 crossref_primary_10_1016_S0892_0362_98_00017_8 crossref_primary_10_1016_0741_8329_93_90007_B crossref_primary_10_1080_13556219872335 crossref_primary_10_1016_S0024_3205_97_01115_6 crossref_primary_10_1111_j_1521_0391_2009_00001_x crossref_primary_10_1520_JFS2005118 crossref_primary_10_3109_15563659609013786 crossref_primary_10_1002__SICI_1098_2396_199705_26_1_11__AID_SYN2_3_0_CO_2_H crossref_primary_10_1124_dmd_104_000554 crossref_primary_10_1038_aps_2017_90 crossref_primary_10_1016_S0165_3806_97_00032_1 crossref_primary_10_1007_s10038_003_0021_7 crossref_primary_10_1016_j_neubiorev_2003_11_009 crossref_primary_10_1016_j_ejps_2009_03_011 crossref_primary_10_1124_pr_57_1_1 crossref_primary_10_1016_S0162_3109_96_00153_1 crossref_primary_10_1016_j_jmb_2006_10_031 crossref_primary_10_5021_ad_2015_27_3_269 crossref_primary_10_1016_0091_3057_94_00378_V crossref_primary_10_1016_0376_8716_93_90109_4 crossref_primary_10_1002_syn_890120308 crossref_primary_10_1016_S0379_0738_99_00222_4 crossref_primary_10_1002_syn_890120307 crossref_primary_10_1016_0378_4274_93_90028_V crossref_primary_10_1093_jat_bky057 crossref_primary_10_3109_08923979509019759 crossref_primary_10_1520_JFS13770J crossref_primary_10_1124_dmd_31_1_16 crossref_primary_10_1124_mol_64_6_1575 crossref_primary_10_1002_jps_2600840704 crossref_primary_10_1002_med_21745 crossref_primary_10_1016_0741_8329_92_90085_O crossref_primary_10_1016_0006_2952_92_90642_V crossref_primary_10_1016_j_bmc_2008_11_008 crossref_primary_10_1016_j_fct_2013_12_013 crossref_primary_10_1080_13556219971632 crossref_primary_10_1016_0376_8716_94_90073_6 crossref_primary_10_1093_clinchem_46_11_1787 crossref_primary_10_1080_00397919208019293 crossref_primary_10_1177_2049463713507439 crossref_primary_10_1007_s40262_014_0160_3 crossref_primary_10_1016_S0735_6757_96_90085_6 crossref_primary_10_1021_js980283h crossref_primary_10_1002_ddr_430330102 crossref_primary_10_1097_00008571_200307000_00008 crossref_primary_10_1007_s00216_021_03596_x crossref_primary_10_1016_S0091_3057_02_00764_5 crossref_primary_10_1016_j_microc_2023_109608 crossref_primary_10_1111_j_1600_0773_1993_tb01331_x crossref_primary_10_1016_S0006_2952_99_00249_X crossref_primary_10_1080_13556219872308 crossref_primary_10_1124_dmd_109_030056 crossref_primary_10_1124_dmd_113_053512 crossref_primary_10_1016_j_bcp_2018_01_028 crossref_primary_10_1016_0735_6757_94_90070_1 crossref_primary_10_1007_BF02466516 crossref_primary_10_1080_02791072_1992_10471648 crossref_primary_10_1186_s40543_023_00412_2 crossref_primary_10_1016_0091_3057_92_90185_I crossref_primary_10_1021_js970072x crossref_primary_10_1177_088307389400900302 crossref_primary_10_1097_00007691_200006000_00006 crossref_primary_10_1016_0378_4347_94_00133_2 crossref_primary_10_1016_1056_8719_93_90052_G crossref_primary_10_1016_j_forsciint_2011_11_001 crossref_primary_10_1016_0006_2952_94_90461_8 crossref_primary_10_1016_0166_4328_96_00077_0 crossref_primary_10_1093_jat_bkr006 crossref_primary_10_1007_BF02246187 crossref_primary_10_23907_2012_032 crossref_primary_10_1002_dta_1993 crossref_primary_10_1016_0379_0738_95_01749_9 crossref_primary_10_1016_0024_3205_96_00227_5 crossref_primary_10_1080_00498250902769967 crossref_primary_10_1016_0378_4347_92_80315_H crossref_primary_10_1002_bdd_1953 crossref_primary_10_1124_mol_111_074534 crossref_primary_10_3109_15563659809162576 crossref_primary_10_1002_pmic_200600041 crossref_primary_10_1007_s11095_013_1158_5 crossref_primary_10_1021_js960026h crossref_primary_10_1097_01_ftd_0000211812_27558_6e crossref_primary_10_1016_0378_4347_95_00525_0 crossref_primary_10_1016_S0379_0738_99_00164_4 crossref_primary_10_1016_j_intimp_2014_10_025 crossref_primary_10_1007_s40262_014_0226_2 crossref_primary_10_1016_S0002_9378_99_70631_9 crossref_primary_10_1038_s41598_019_51580_4 crossref_primary_10_1002_hep_1840180522 crossref_primary_10_1016_0731_7085_95_01284_R crossref_primary_10_1016_S0033_0620_97_80023_0 crossref_primary_10_1016_j_ympev_2010_05_018 crossref_primary_10_1016_0162_3109_95_00042_R crossref_primary_10_1016_S0024_3205_99_00159_9 crossref_primary_10_1016_S1359_6446_05_03383_0 crossref_primary_10_1177_0269881107079170 crossref_primary_10_1016_0009_2797_92_90127_7 crossref_primary_10_1016_j_forsciint_2005_04_017 crossref_primary_10_1016_j_ntt_2004_10_001 crossref_primary_10_1097_00006842_199909000_00007 crossref_primary_10_1097_00007691_199810000_00019 crossref_primary_10_1007_s00216_010_4449_2 crossref_primary_10_1016_S0300_483X_98_00081_X crossref_primary_10_1016_0041_008X_92_90210_J crossref_primary_10_1520_JFS13909J crossref_primary_10_1124_jpet_113_206383 crossref_primary_10_1021_js950437i crossref_primary_10_1016_0278_5846_96_00034_6 crossref_primary_10_1016_j_vascn_2007_11_003 crossref_primary_10_3109_15563659809162614 crossref_primary_10_1016_S0733_8627_05_70197_8 |
| ContentType | Journal Article |
| DBID | CGR CUY CVF ECM EIF NPM |
| DOI | 10.1096/fasebj.5.12.1916095 |
| DatabaseName | Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed |
| DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) |
| DatabaseTitleList | MEDLINE |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database |
| DeliveryMethod | no_fulltext_linktorsrc |
| Discipline | Biology |
| ExternalDocumentID | 1916095 |
| Genre | Research Support, U.S. Gov't, P.H.S Journal Article |
| GrantInformation_xml | – fundername: NIAAA NIH HHS grantid: P50-AA07611 |
| GroupedDBID | --- -DZ -~X .55 0R~ 0VX 123 18M 1OB 1OC 29H 2WC 33P 34G 39C 3O- 4.4 53G 5GY 5RE 85S AAHHS AANLZ ABCUV ABDNZ ABEFU ABJNI ABOCM ACCFJ ACCZN ACGFS ACIWK ACNCT ACPOU ACPRK ACXQS ACYGS ADKYN ADZMN AEEZP AEIGN AENEX AEQDE AEUYR AFFNX AFFPM AFRAH AGCDD AHBTC AI. AITYG AIURR AIWBW AIZAD AJBDE ALMA_UNASSIGNED_HOLDINGS ALUQN AMYDB BFHJK BIYOS C1A CGR CS3 CUY CVF DCZOG DU5 D~5 E3Z EBS ECM EIF EJD F20 F5P F9R FRP H13 HGLYW HZ~ H~9 J5H L7B LATKE LEEKS MEWTI MVM NEJ NPM O9- OHT OVD Q-A RHF RHI RJQFR ROL SAMSI SJN SUPJJ TEORI TFA TR2 TWZ VH1 W8F WH7 WHG WOQ WXSBR X7M XJT XOL XSW Y6R YBU YCJ YHG YKV YNH YSK Z0Y ZCA ZE2 ZGI ZXP ~KM |
| ID | FETCH-LOGICAL-c5126-be20b3862e6c98d09f2acc84253077d7f229f60a7d6849e83901a9eff41f73432 |
| ISSN | 0892-6638 |
| IngestDate | Sat Sep 28 08:40:37 EDT 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 12 |
| Language | English |
| LinkModel | OpenURL |
| MergedId | FETCHMERGED-LOGICAL-c5126-be20b3862e6c98d09f2acc84253077d7f229f60a7d6849e83901a9eff41f73432 |
| PMID | 1916095 |
| ParticipantIDs | pubmed_primary_1916095 |
| PublicationCentury | 1900 |
| PublicationDate | September 1991 |
| PublicationDateYYYYMMDD | 1991-09-01 |
| PublicationDate_xml | – month: 09 year: 1991 text: September 1991 |
| PublicationDecade | 1990 |
| PublicationPlace | United States |
| PublicationPlace_xml | – name: United States |
| PublicationTitle | The FASEB journal |
| PublicationTitleAlternate | FASEB J |
| PublicationYear | 1991 |
| SSID | ssj0001016 |
| Score | 1.8407321 |
| Snippet | A new, pharmacologically active metabolite of cocaine, ethylcocaine, has been reported in individuals after concurrent use of cocaine and ethanol. Formation of... |
| SourceID | pubmed |
| SourceType | Index Database |
| StartPage | 2735 |
| SubjectTerms | Carboxylic Ester Hydrolases - isolation & purification Carboxylic Ester Hydrolases - metabolism Chromatography, Gel Cocaine - analogs & derivatives Cocaine - chemistry Cocaine - metabolism Ethanol - metabolism Gas Chromatography-Mass Spectrometry Humans Liver - enzymology Molecular Structure Molecular Weight |
| Title | Human liver cocaine esterases: ethanol-mediated formation of ethylcocaine |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/1916095 |
| Volume | 5 |
| hasFullText | |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LTwIxEG5QQ-LF-CK-04M3ssh2n_WGRqImchEiJ0l32yYaBA540F_vTFvXBjVBL5ulLZtl5mP2m-nMLCGncRKqNNR5ECWqCOKo4IGQIoSPnMmIRSpPsd75rpdeD-LbYTKs1R69rKXXedEq33-sK_mPVmEM9IpVsn_QbHVRGIBz0C8cQcNwXErHNgI_xtSKJhg2gYzRdD6AR5NJdVMYGJ-OA1MfgtyyqlVEkgizb2P3PZ-kInS6nfuri6Z_F8h2lds1-oqA2uYET3bczx8W2HbYLq52oy6mQNTNygeXUSxdAV5YJVRVZomzAHhK7tvQxIcK8w1iZruRfLPU4DqheEEexXMrwZAseI7Y_c5fDZKavRjlLTu50DzbzayQlSxHK9jDWI57TmPcwvgY7vd89qTi6dkPt7VO6u5swQExRKS_STacB0E7Fg5bpKYm26Ru3yn6tkNuDCioAQV1yqUVKM7pIiRoBQk61dSHxC4ZdK_6l9eBe19GUAJtS4NCsXYRgYuq0pLnss01E2WJ-6xgyDOZaca4Ttsik2kec5VjuEtwpXUc6gwLjBtkdTKdqD1CZQncryyTtmY8loUQ2MeRa_DtZZwwpfdJw8pgNLNNUUZOOAe_TRyS9S80HZE1Df9BdQyEbl6cGL18ADYwRmo |
| link.rule.ids | 783 |
| linkProvider | National Library of Medicine |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Human+liver+cocaine+esterases%3A+ethanol-mediated+formation+of+ethylcocaine&rft.jtitle=The+FASEB+journal&rft.au=Dean%2C+R+A&rft.au=Christian%2C+C+D&rft.au=Sample%2C+R+H&rft.au=Bosron%2C+W+F&rft.date=1991-09-01&rft.issn=0892-6638&rft.volume=5&rft.issue=12&rft.spage=2735&rft_id=info:doi/10.1096%2Ffasebj.5.12.1916095&rft_id=info%3Apmid%2F1916095&rft_id=info%3Apmid%2F1916095&rft.externalDocID=1916095 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0892-6638&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0892-6638&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0892-6638&client=summon |