Dextrothyroxine

Dextrothyroxine
Clinical data

Trade names	Choloxin
AHFS/Drugs.com	Multum Consumer Information
Pregnancy category	US: B (No risk in non-human studies)
ATC code	C10AX01 (WHO)
Legal status
Legal status	Discontinued
Identifiers
IUPAC name (2R)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
Synonyms	D-3,5,3',5'-tetraiodothyronine
CAS Number	51-49-0
PubChem (CID)	8730
DrugBank	DB00509
ChemSpider	8402
UNII	4W9K63FION
ChEBI	CHEBI:30659
ChEMBL	CHEMBL559
ECHA InfoCard	100.000.094
Chemical and physical data
Formula	C₁₅H₁₁I₄NO₄
Molar mass	776.87 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)[C@H](N)Cc2cc(I)c(Oc1cc(I)c(O)c(I)c1)c(I)c2
InChI InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m1/s1 Key:XUIIKFGFIJCVMT-GFCCVEGCSA-N

Dextrothyroxine (trade name Choloxin) saw research as a cholesterol-lowering drug^[1]^[2] but was pulled due to cardiac side-effects. It also increases hepatic lipase which in turn improves utilization of triglycerides, improving apolipoprotein E cholesterol particles.

References

↑ Bantle, J. P.; Hunninghake, D. B.; Frantz, I. D.; Kuba, K.; Mariash, C. N.; Oppenheimer, J. H. (1984). "Comparison of effectiveness of thyrotropin-suppressive doses of D- and L-thyroxine in treatment of hypercholesterolemia". The American Journal of Medicine. 77 (3): 475–481. doi:10.1016/0002-9343(84)90107-4. PMID 6475988.
↑ Bommer, C.; Werle, E.; Walter-Sack, I.; Keller, C.; Gehlen, F.; Wanner, C.; Nauck, M.; März, W.; Wieland, H.; Bommer, J. (1998). "D-thyroxine reduces lipoprotein(a) serum concentration in dialysis patients". Journal of the American Society of Nephrology : JASN. 9 (1): 90–96. PMID 9440092.

Lipid modifying agents (C10)

GI tract

Cholesterol absorption inhibitors, NPC1L1	Ezetimibe SCH-48461

Bile acid sequestrants/resins (LDL)	Colestyramine Colestipol Colestilan Colextran Colesevelam

Liver

Statins (HMG-CoA reductase, LDL)	Simvastatin^# Atorvastatin Fluvastatin Lovastatin Mevastatin Pitavastatin Pravastatin Rosuvastatin Cerivastatin^‡

Niacin and derivatives (HDL and LDL)	Niceritrol Niacin Nicofuranose Aluminium nicotinate Nicotinyl alcohol Acipimox

MTTP inhibitors (VLDL)	Dirlotapide Lomitapide Mitratapide

Blood vessels

Fibrates (PPAR)	Clofibrate^‡ Bezafibrate Aluminium clofibrate Gemfibrozil Fenofibrate Simfibrate Ronifibrate Ciprofibrate Etofibrate Clofibride Clinofibrate

CETP inhibitors (HDL)	Anacetrapib^† Dalcetrapib^§ Evacetrapib^§ Torcetrapib^§

Combinations

Other

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Nuclear receptor modulators

CAR

Agonists	5β-Dihydroprogesterone 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole Cyclophosphamide Cypermethrin DHEA Efavirenz Ellagic acid Griseofulvin Methoxychlor Mifepristone Nefazodone Nevirapine Nicardipine Octicizer Permethrin Phenobarbital Phenytoin Reserpine TCPOBOP Telmisartan Tolnaftate Troglitazone Valproic acid

Antagonists	3,17β-Estradiol 3α-Androstanol 3α-Androstenol 3β-Androstanol 17-Androstanol AITC Ethinyl estradiol Meclizine Nigramide J Okadaic acid PK-11195 S-07662 T-0901317

ERR

ERRα

Agonists	6,3′,4′-Trihydroxyflavone Biochanin A Cholesterol Daidzein Genistein

Antagonists	Diethylstilbestrol XCT-790

ERRβ

Agonists	DY-131 (GSK-9089) GSK-4716 (GW-4716)

Antagonists	4-Hydroxytamoxifen (afimoxifene) Diethylstilbestrol

ERRγ

Agonists	Bisphenol A DY-131 (GSK-9089) GSK-4716 (GW-4716)

Antagonists	4-Hydroxytamoxifen (afimoxifene) Diethylstilbestrol

FXR

Agonists	Bile acids Cafestol Chenodeoxycholic acid Fexaramine GW-4064 Obeticholic acid

Antagonists	Guggulsterone

LXR

Agonists	22R-Hydroxycholesterol 24S-Hydroxycholesterol 27-Hydroxycholesterol Cholestenoic acid DMHCA GW-3965 Hypocholamide T-0901317

Antagonists	Efavirenz

PPAR

PPARα

Agonists	15-HETE 15-HpETE Aleglitazar Aluminium clofibrate Arachidonic acid Bezafibrate Clofibrate CP-775146 Daidzein DHEA Elafibranor Etomoxir Fenofibrate Genistein Gemfibrozil GW-7647 Leukotriene B₄ LG-101506 LG-100754 Lobeglitazone Muraglitazar Oleylethanolamide Palmitoylethanolamide Pemafibrate Perfluorononanoic acid Perfluorooctanoic acid Pioglitazone Saroglitazar Sodelglitazar Tesaglitazar Tetradecylthioacetic acid Troglitazone WY-14643

Antagonists	GW-6471 MK-886

PPARδ

Agonists	15-HETE 15-HpETE Arachidonic acid Bezafibrate Daidzein Elafibranor Fonadelpar Genistein GW-0742 GW-501516 L-165,041 LG-101506 MBX-8025 Sodelglitazar Tetradecylthioacetic acid

Antagonists	FH-535 GSK-0660 GSK-3787

PPARγ

Agonists	5-Oxo-ETE 5-Oxo-15-hydroxy-ETE 15-Deoxy-Δ^12,14-prostaglandin J₂ 15-HETE 15-HpETE Aleglitazar Arachidonic acid Balaglitazone Berberine Bezafibrate Cevoglitazar Ciglitazone Daidzein Darglitazone Edaglitazone Efatutazone Englitazone Etalocib Farglitazar Genistein GW-1929 Ibuprofen Imiglitazar Indeglitazar LG-100268 LG-100754 LG-101506 Lobeglitazone Muraglitazar (muroglitazar) nTZDpa Naveglitazar Netoglitazone Oxeglitazar Peliglitazar Pemaglitazar Perfluorononanoic acid Pioglitazone Prostaglandin J₂ Ragaglitazar Reglitazar Rivoglitazone Rosiglitazone RS5444 Saroglitazar Sipoglitazar Sodelglitazar Telmisartan Tesaglitazar Troglitazone

SPPARMs	BADGE EPI-001 INT-131 MK-0533 S26948

Antagonists	FH-535 GW-9662 SR-202 T-0070907

Unknown	SR-1664

Unselective

Agonists	Ciprofibrate Clinofibrate Clofibride Englitazone Etofibrate Farglitazar Netoglitazone Ronifibrate Rivoglitazone Simfibrate

Unsorted

Agonists	Seladelpar

PXR

Agonists	5α-Dihydroprogesterone 5β-Dihydroprogesterone 17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Δ⁴-Androstenedione Δ⁵-Androstenediol Δ⁵-Androstenedione AA-861 Allopregnanolone Alpha-Lipoic acid Ambrisentan AMI-193 Amlodipine besylate Antimycotics Artemisinin Aurothioglucose Bile acids Bithionol Bosentan Bumecaine Cafestol Cephaloridine Cephradine Chlorpromazine Ciglitazone Clindamycin Clofenvinfos Chloroxine Clotrimazole Colforsin Corticosterone Cyclophosphamide Cyproterone acetate Demecolcine Dexamethasone DHEA DHEA-S Dibunate sodium Diclazuril Dicloxacillin Dimercaprol Dinaline Docetaxel Docusate calcium Dodecylbenzenesulfonic acid Dronabinol Droxidopa Eburnamonine Ecopipam Enzacamene Epothilone B Erythromycin Famprofazone Febantel Felodipine Fenbendazole Fentanyl Flucloxacillin Fluorometholone Griseofulvin Guggulsterone Haloprogin Hetacillin potassium Hyperforin Hypericum perforatum (St John's wort) Indinavir sulfate Lasalocid sodium Levothyroxine Linolenic acid LOE-908 Loratadine Lovastatin Meclizine Methacycline Methylprednisolone Metyrapone Mevastatin Mifepristone Nafcillin Nicardipine Nicotine Nifedipine Nilvadipine Nisoldipine Norelgestromin Omeprazole Orlistat Oxatomide Paclitaxel Phenobarbital Piperine Plicamycin Prednisolone Pregnanolone Pregnenolone Pregnenolone 16α-carbonitrile Proadifen Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine SR-12813 Suberoylanilide Sulfisoxazole Suramin Tacrolimus Tenylidone Terconazole Testosterone isocaproate Tetracycline Thiamylal sodium Thiothixene Thonzonium bromide Tianeptine Troglitazone Troleandomycin Tropanyl 3,5-dimethulbenzoate Zafirlukast Zearalanol

Antagonists	Ketoconazole Sesamin

RAR

Agonists	9CDHRA 9-cis-Retinoic acid (alitretinoin) AC-261066 AC-55649 Acitretin Adapalene all-trans-Retinoic acid (tretinoin) AM-580 BMS-493 BMS-753 BMS-961 CD-1530 CD-2314 CD-437 Ch-55 EC 23 Etretinate Fenretinide Isotretinoin Palovarotene Retinoic acid Retinol (vitamin A) Tamibarotene Tazarotene Tazarotenic acid TTNPB

Antagonists	BMS-195614 BMS-493 CD-2665 ER-50891 LE-135 MM-11253

Others	Retinoic acid metabolism inhibitors: Liarozole

RXR

Agonists	9CDHRA 9-cis-Retinoic acid (alitretinoin) all-trans-Retinoic acid (tretinoin) Bexarotene CD 3254 Docosahexaenoic acid Fluorobexarotene Isotretinoin LG-100268 LG-101506 LG-100754 Retinoic acid Retinol (vitamin A) SR-11237

Antagonists	HX-531 HX-630 LG-100754 PA-452 UVI-3003

SHR

See here instead.

VDR

Agonists	7-Dehydrocholesterol 22-Oxacalcitriol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin D₃) Dihydrotachysterol Doxercalciferol EB-1089 Eldecalcitol Ercalcidiol Ercalcitriol Ergocalciferol (vitamin D₂) Lithocholic acid Paricalcitol Tacalcitol

Agonists	Dextrothyroxine DITPA Eprotirome (KB-2115) KB-2611 KB-130015 Levothyroxine Liothyronine MB-07811 MGL-3196 (VIA-3196) Sobetirome (GC-1, GRX-431) Thyroxine Tiratricol Triiodothyronine VK-0214 VK-2809 ZYT1

Others	Carrier proteins: Albumin Thyroxine-binding globulin Transthyretin

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Dextrothyroxine

See also

References