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Chemical Compound Review

heptoate     heptanoate

Synonyms: enanthate, heptylate, Heptanoate, oenanthate, enanthylate, ...
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Disease relevance of enanthic acid

  • Pretreatment of rats for 6 weeks plus continued treatment during procarbazine administration with testosterone enanthate, 240 micrograms/100 g body weight, resulted in a marked protection of spermatogenesis [1].
  • These men were classified into groups according to whether 6 months of weekly T enanthate injections produced azoospermia (n = 54), near-azoospermia (n = 7), and nonazoospermia (n = 14) [2].
  • Sixty-nine men with primary and 62 with secondary hypogonadism began substitution therapy with im injections of T enanthate (n = 81), transdermal T preparations (n = 19), sc injections of human chorionic gonadotropin (n = 17), or oral T undecanoate (n = 14) for 2.4 +/- 0.8 yr [3].
  • To further evaluate the mechanism of the effect of DHT on plasma GH, seven male subjects with adolescent gynecomastia were treated with DHT heptanoate, and their responses were studied at 1 week and 3.5 months [4].
  • In an attempt to improve virilization, high dose testosterone enanthate treatment (250 mg by i.m. injection once a week) was begun [5].

Psychiatry related information on enanthic acid


High impact information on enanthic acid


Chemical compound and disease context of enanthic acid


Biological context of enanthic acid


Anatomical context of enanthic acid


Associations of enanthic acid with other chemical compounds


Gene context of enanthic acid

  • Testosterone enanthate therapy is effective and independent of SRD5A2 and AR gene polymorphisms in boys with micropenis [35].
  • The activities of LPL and HL in postheparin plasma were markedly increased by 1 week after a testosterone enanthate injection (P less than 0.001) [36].
  • The SHBG in four subjects treated with norethindrone enanthate fell within our normal range for men, and the mean serum testosterone levels fell 40% below the normal basal levels in these cases [37].
  • This report documents exacerbation of a PRL-secreting tumor after two separate 200-mg testosterone enanthate (T) injections despite continued bromocriptine (BRC) therapy [38].
  • To determine whether more nearly physiological levels of human LH (hLH) also can stimulate spermatogenesis when FSH levels are suppressed, we administered hLH to normal men whose endogenous gonadotropin levels and sperm production were suppressed by exogenous testosterone enanthate (T) [39].

Analytical, diagnostic and therapeutic context of enanthic acid


  1. Protection from procarbazine-induced damage of spermatogenesis in the rat by androgen. Delic, J.I., Bush, C., Peckham, M.J. Cancer Res. (1986) [Pubmed]
  2. Pharmacogenetic polymorphisms of the AR and metabolism and susceptibility to hormone-induced azoospermia. Yu, B., Handelsman, D.J. J. Clin. Endocrinol. Metab. (2001) [Pubmed]
  3. Prostate volume and growth in testosterone-substituted hypogonadal men are dependent on the CAG repeat polymorphism of the androgen receptor gene: a longitudinal pharmacogenetic study. Zitzmann, M., Depenbusch, M., Gromoll, J., Nieschlag, E. J. Clin. Endocrinol. Metab. (2003) [Pubmed]
  4. Androgen-stimulated pubertal growth: the effects of testosterone and dihydrotestosterone on growth hormone and insulin-like growth factor-I in the treatment of short stature and delayed puberty. Keenan, B.S., Richards, G.E., Ponder, S.W., Dallas, J.S., Nagamani, M., Smith, E.R. J. Clin. Endocrinol. Metab. (1993) [Pubmed]
  5. Response to androgen treatment in a patient with partial androgen insensitivity and a mutation in the deoxyribonucleic acid-binding domain of the androgen receptor. Weidemann, W., Peters, B., Romalo, G., Spindler, K.D., Schweikert, H.U. J. Clin. Endocrinol. Metab. (1998) [Pubmed]
  6. Comparison of the incidence and severity of extrapyramidal side effects with fluphenazine enanthate and fluphenazine decanoate. Kane, J., Quitkin, F., Rifkin, A., Klein, D.F. The American journal of psychiatry. (1978) [Pubmed]
  7. The use of depot neuroleptics: clinical experience in the United States. Kane, J.M. The Journal of clinical psychiatry. (1984) [Pubmed]
  8. Fluphenazine enanthate in the outpatient treatment of late paraphrenia. Raskind, M., Alvarez, C., Herlin, S. Journal of the American Geriatrics Society. (1979) [Pubmed]
  9. A new class of long-acting hormonal steroid preparation: synthesis of dimeric androgenes coupled at C3-C3 and C17-C3 and of an androgen-progestogen combination. Kuhl, H., Taubert, H.D. Steroids (1976) [Pubmed]
  10. Testosterone treatment in adolescent boys with constitutional delay in growth and development. Richman, R.A., Kirsch, L.R. N. Engl. J. Med. (1988) [Pubmed]
  11. Fluphenazine enanthate and fluphenazine decanoate in the treatment of schizophrenic outpatients: extrapyramidal symptoms and therapeutic effect. Chouinard, G., Annable, L., Ross-Chouinard, A. The American journal of psychiatry. (1982) [Pubmed]
  12. Androgen receptor in human skeletal muscle and cultured muscle satellite cells: up-regulation by androgen treatment. Sinha-Hikim, I., Taylor, W.E., Gonzalez-Cadavid, N.F., Zheng, W., Bhasin, S. J. Clin. Endocrinol. Metab. (2004) [Pubmed]
  13. Effects of GH and/or sex steroid administration on abdominal subcutaneous and visceral fat in healthy aged women and men. Münzer, T., Harman, S.M., Hees, P., Shapiro, E., Christmas, C., Bellantoni, M.F., Stevens, T.E., O'Connor, K.G., Pabst, K.M., St Clair, C., Sorkin, J.D., Blackman, M.R. J. Clin. Endocrinol. Metab. (2001) [Pubmed]
  14. Pharmacokinetics, efficacy, and safety of a permeation-enhanced testosterone transdermal system in comparison with bi-weekly injections of testosterone enanthate for the treatment of hypogonadal men. Dobs, A.S., Meikle, A.W., Arver, S., Sanders, S.W., Caramelli, K.E., Mazer, N.A. J. Clin. Endocrinol. Metab. (1999) [Pubmed]
  15. Testosterone treatment in adolescents with delayed puberty: changes in body composition, protein, fat, and glucose metabolism. Arslanian, S., Suprasongsin, C. J. Clin. Endocrinol. Metab. (1997) [Pubmed]
  16. Ethopropazine and benztropine in neuroleptic-induced parkinsonism. Chouinard, G., Annable, L., Ross-Chouinard, A., Kropsky, M.L. The Journal of clinical psychiatry. (1979) [Pubmed]
  17. Intramuscular testosterone enanthate plus very low dosage oral levonorgestrel suppresses spermatogenesis without causing weight gain in normal young men: a randomized clinical trial. Anawalt, B.D., Amory, J.K., Herbst, K.L., Coviello, A.D., Page, S.T., Bremner, W.J., Matsumoto, A.M. J. Androl. (2005) [Pubmed]
  18. Attainment and maintenance of azoospermia with combined monthly injections of depot medroxyprogesterone acetate and testosterone enanthate. Alvarez-Sanchez, F., Faundes, A., Brache, V., Leon, P. Contraception. (1977) [Pubmed]
  19. Depot perphenazine decanoate and enanthate for schizophrenia. Quraishi, S., David, A. Cochrane database of systematic reviews (Online) (2000) [Pubmed]
  20. Dihydrotestosterone heptanoate: synthesis, pharmacokinetics, and effects on hypothalamic-pituitary-testicular function. Keenan, B.S., Eberle, A.J., Sparrow, J.T., Greger, N.G., Panko, W.B. J. Clin. Endocrinol. Metab. (1987) [Pubmed]
  21. Pharmacokinetic characteristics, efficacy, and safety of buccal testosterone in hypogonadal males: a pilot study. Dobs, A.S., Hoover, D.R., Chen, M.C., Allen, R. J. Clin. Endocrinol. Metab. (1998) [Pubmed]
  22. Body composition and muscle strength in healthy men receiving testosterone enanthate for contraception. Young, N.R., Baker, H.W., Liu, G., Seeman, E. J. Clin. Endocrinol. Metab. (1993) [Pubmed]
  23. Germ cell survival, differentiation, and epididymal transit kinetics in mouse testis subjected to high in vivo levels of testosterone enanthate. Goldberg, R.B. Cell Tissue Res. (1984) [Pubmed]
  24. Aerobic biological treatment of synthetic municipal wastewater in membrane-coupled bioreactors. Klatt, C.G., LaPara, T.M. Biotechnol. Bioeng. (2003) [Pubmed]
  25. Suppression of spermatogenesis in man induced by Nal-Glu gonadotropin releasing hormone antagonist and testosterone enanthate (TE) is maintained by TE alone. Swerdloff, R.S., Bagatell, C.J., Wang, C., Anawalt, B.D., Berman, N., Steiner, B., Bremner, W.J. J. Clin. Endocrinol. Metab. (1998) [Pubmed]
  26. Administration of 5alpha-androstane-3alpha,17beta-diol to female tammar wallaby pouch young causes development of a mature prostate and male urethra. Leihy, M.W., Shaw, G., Renfree, M.B., Wilson, J.D. Endocrinology (2002) [Pubmed]
  27. Effect of 13-cis-retinoic acid on the hamster flank organ. Gomez, E.C., Moskowitz, R.J. J. Invest. Dermatol. (1980) [Pubmed]
  28. Effect of testosterone enanthate on testis size. Palacios, A., McClure, R.D., Campfield, A., Swerdloff, R.S. J. Urol. (1981) [Pubmed]
  29. Oligozoospermia induced by exogenous testosterone is associated with normal functioning residual spermatozoa. Wang, C., Leung, A., Superlano, L., Steiner, B., Swerdloff, R.S. Fertil. Steril. (1997) [Pubmed]
  30. Potential of testosterone buciclate for male contraception: endocrine differences between responders and nonresponders. Behre, H.M., Baus, S., Kliesch, S., Keck, C., Simoni, M., Nieschlag, E. J. Clin. Endocrinol. Metab. (1995) [Pubmed]
  31. Testosterone-induced muscle hypertrophy is associated with an increase in satellite cell number in healthy, young men. Sinha-Hikim, I., Roth, S.M., Lee, M.I., Bhasin, S. Am. J. Physiol. Endocrinol. Metab. (2003) [Pubmed]
  32. Hormonal regulation of somatostatin messenger RNA. Baldino, F., Fitzpatrick-McElligott, S., O'Kane, T.M., Gozes, I. Synapse (1988) [Pubmed]
  33. Release and elimination of 14C-fluphenazine enanthate and decanoate esters administered in sesame oil to dogs. Dreyfuss, J., Ross, J.J., Shaw, J.M., Miller, I., Schreiber, E.C. Journal of pharmaceutical sciences. (1976) [Pubmed]
  34. Serum copper and zinc in hormonal contraceptive users. Prema, K., Ramalakshmi, B.A., Babu, S. Fertil. Steril. (1980) [Pubmed]
  35. Testosterone enanthate therapy is effective and independent of SRD5A2 and AR gene polymorphisms in boys with micropenis. Ishii, T., Sasaki, G., Hasegawa, T., Sato, S., Matsuo, N., Ogata, T. J. Urol. (2004) [Pubmed]
  36. Testosterone substitution increases the activity of lipoprotein lipase and hepatic lipase in hypogonadal males. Sorva, R., Kuusi, T., Taskinen, M.R., Perheentupa, J., Nikkilä, E.A. Atherosclerosis (1988) [Pubmed]
  37. Effects of progestin-estrogen combination and progestational contraceptives on pituitary gonadotropins, gonadal steroids and sex hormone-binding globulin. Tafurt, C.A., Sobrevilla, L.A., de Estrada, R. Fertil. Steril. (1980) [Pubmed]
  38. Testosterone-related exacerbation of a prolactin-producing macroadenoma: possible role for estrogen. Prior, J.C., Cox, T.A., Fairholm, D., Kostashuk, E., Nugent, R. J. Clin. Endocrinol. Metab. (1987) [Pubmed]
  39. Stimulation of sperm production by human luteinizing hormone in gonadotropin-suppressed normal men. Matsumoto, A.M., Paulsen, C.A., Bremner, W.J. J. Clin. Endocrinol. Metab. (1984) [Pubmed]
  40. Contrasting effects of testosterone and stanozolol on serum lipoprotein levels. Thompson, P.D., Cullinane, E.M., Sady, S.P., Chenevert, C., Saritelli, A.L., Sady, M.A., Herbert, P.N. JAMA (1989) [Pubmed]
  41. Modulation of pulsatile gonadotropin secretion by testosterone in man. Matsumoto, A.M., Bremner, W.J. J. Clin. Endocrinol. Metab. (1984) [Pubmed]
  42. Establishing the minimum effective dose and additive effects of depot progestin in suppression of human spermatogenesis by a testosterone depot. Handelsman, D.J., Conway, A.J., Howe, C.J., Turner, L., Mackey, M.A. J. Clin. Endocrinol. Metab. (1996) [Pubmed]
  43. Effects of chronic testosterone administration in normal men: safety and efficacy of high dosage testosterone and parallel dose-dependent suppression of luteinizing hormone, follicle-stimulating hormone, and sperm production. Matsumoto, A.M. J. Clin. Endocrinol. Metab. (1990) [Pubmed]
  44. Do androgens regulate growth hormone-binding protein in adult man? Ip, T.P., Hoffman, D.M., O'Sullivan, A.J., Leung, K.C., Ho, K.K. J. Clin. Endocrinol. Metab. (1995) [Pubmed]
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